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1923833-60-6

  • Product Name:BMS-986205
  • Molecular Weight:410.919
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Product Details

Purity:99%

Factory supply BMS-986205 1923833-60-6 with sufficient stock and high standard

  • Molecular Formula:C24H24ClFN2O
  • Molecular Weight:410.919
  • Boiling Point:606.8±45.0 °C(Predicted) 
  • PKA:13.80±0.70(Predicted) 
  • Density:1?+-.0.06 g/cm3(Predicted) 

1923833-60-6 Relevant articles

Rapid Development of a Commercial Process for Linrodostat, an Indoleamine 2,3-Dioxygenase (IDO) Inhibitor

Fraunhoffer, Kenneth J.,Delmonte, Albert J.,Beutner, Gregory L.,Bultman, Michael S.,Camacho, Kathryn,Cohen, Benjamin,Dixon, Darryl D.,Fan, Yu,Fanfair, Dayne,Freitag, Adam J.,Glace, Andrew W.,Gonzalez-Bobes, Francisco,Gujjar, Manjunath,Haley, Matthew W.,Hickey, Matthew R.,Ho, Jeanne,Iyer, Vidya,Maity, Prantik,Patel, Sunil,Rosso, Victor W.,Schmidt, Michael A.,Stevens, Jason M.,Tan, Yichen,Wilbert, Christopher,Young, Ian S.,Yu, Miao

, p. 2482 - 2498 (2019)

The process development and the kilogram...

FORMULATED AND/OR CO-FORMULATED LIPOSOME COMPOSITIONS CONTAINING IDO ANTAGONIST PRODRUGS USEFUL IN THE TREATMENT OF CANCER AND METHODS THEREOF

-

, (2021/05/21)

Formulated and/or co-formulated liposome...

IMMUNOREGULATORY AGENTS

-

, (2016/06/01)

Compounds that modulate the oxidoreducta...

1923833-60-6 Process route

cyclohexanedione monoethylene ketal
4746-97-8

cyclohexanedione monoethylene ketal

(R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide
1923833-60-6

(R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide

Conditions
Conditions Yield
Multi-step reaction with 12 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C
1.2: 0.5 h / 0 - 20 °C
2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 2585.81 Torr / Inert atmosphere
3.1: hydrogenchloride / water; acetone / 2 h / Reflux
4.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 20 °C / Inert atmosphere
5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere
6.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 16 h / 100 °C / Sealed tube; Inert atmosphere
7.1: palladium on activated charcoal; ammonium formate / methanol / 1 h / Reflux
8.1: lithium hydroxide; water / ethanol / 6 h / 50 °C
9.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 1.25 h / -78 - 0 °C / Inert atmosphere
9.2: 3.25 h / -78 - 20 °C
10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C
10.2: -50 - -20 °C
11.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 - 20 °C
12.1: propylphosphonic anhydride; pyridine / ethyl acetate / 0.08 h / 20 °C
12.2: 20 °C
With pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methylpyridine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon; palladium on activated charcoal; propylphosphonic anhydride; water; hydrogen; dihydrogen peroxide; ammonium formate; potassium acetate; sodium hexamethyldisilazane; pivaloyl chloride; sodium hydride; potassium carbonate; triethylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; mineral oil;
Multi-step reaction with 12 steps
1.1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2.1: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4.1: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6.1: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one / 16 h / 85 °C
8.1: methanesulfonic acid / water; sulfolane / 14 h / 55 - 105 °C / Industrial scale
8.2: 25 °C / Industrial scale
9.1: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10.1: tetrahydrofuran / -20 °C / Industrial scale
11.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12.1: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; methanesulfonic acid; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; triethylamine; lithium chloride; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; sulfolane; ethanol; tert-butyl methyl ether; water; acetonitrile;
Multi-step reaction with 12 steps
1.1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2.1: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4.1: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6.1: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7.1: sodium tert-pentoxide / toluene / 12 h / 35 - 85 °C / Industrial scale
8.1: methanesulfonic acid / water; sulfolane / 14 h / 55 - 105 °C / Industrial scale
8.2: 25 °C / Industrial scale
9.1: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10.1: tetrahydrofuran / -20 °C / Industrial scale
11.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12.1: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; methanesulfonic acid; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; sodium tert-pentoxide; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; triethylamine; lithium chloride; lithium hydroxide; In tetrahydrofuran; sulfolane; ethanol; tert-butyl methyl ether; water; toluene; acetonitrile;
Multi-step reaction with 12 steps
1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7: sodium t-butanolate / 1-methyl-pyrrolidin-2-one / 16 h / 85 °C
8: acetic acid / water / 130 °C
9: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10: tetrahydrofuran / -20 °C / Industrial scale
11: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; acetic acid; triethylamine; lithium chloride; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; tert-butyl methyl ether; water; acetonitrile;
Multi-step reaction with 12 steps
1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7: sodium tert-pentoxide / toluene / 12 h / 35 - 85 °C / Industrial scale
8: acetic acid / water / 130 °C
9: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10: tetrahydrofuran / -20 °C / Industrial scale
11: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; sodium tert-pentoxide; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; acetic acid; triethylamine; lithium chloride; lithium hydroxide; In tetrahydrofuran; ethanol; tert-butyl methyl ether; water; toluene; acetonitrile;
4-bromine-6-fluoroquinoline
661463-17-8

4-bromine-6-fluoroquinoline

(R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide
1923833-60-6

(R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide

Conditions
Conditions Yield
Multi-step reaction with 12 steps
1.1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2.1: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4.1: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6.1: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one / 16 h / 85 °C
8.1: methanesulfonic acid / water; sulfolane / 14 h / 55 - 105 °C / Industrial scale
8.2: 25 °C / Industrial scale
9.1: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10.1: tetrahydrofuran / -20 °C / Industrial scale
11.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12.1: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; methanesulfonic acid; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; triethylamine; lithium chloride; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; sulfolane; ethanol; tert-butyl methyl ether; water; acetonitrile;
Multi-step reaction with 12 steps
1.1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2.1: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4.1: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6.1: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7.1: sodium tert-pentoxide / toluene / 12 h / 35 - 85 °C / Industrial scale
8.1: methanesulfonic acid / water; sulfolane / 14 h / 55 - 105 °C / Industrial scale
8.2: 25 °C / Industrial scale
9.1: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10.1: tetrahydrofuran / -20 °C / Industrial scale
11.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12.1: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; methanesulfonic acid; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; sodium tert-pentoxide; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; triethylamine; lithium chloride; lithium hydroxide; In tetrahydrofuran; sulfolane; ethanol; tert-butyl methyl ether; water; toluene; acetonitrile;
Multi-step reaction with 12 steps
1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7: sodium t-butanolate / 1-methyl-pyrrolidin-2-one / 16 h / 85 °C
8: acetic acid / water / 130 °C
9: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10: tetrahydrofuran / -20 °C / Industrial scale
11: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; acetic acid; triethylamine; lithium chloride; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; tert-butyl methyl ether; water; acetonitrile;
Multi-step reaction with 12 steps
1: n-butyllithium / tert-butyl methyl ether / 4 h / -75 - -10 °C / Industrial scale
2: thionyl chloride; pyridine / 0.5 h / 5 - 15 °C / Industrial scale
3: hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 80 h / 30 - 35 °C / 1125.11 - 1500.15 Torr / Industrial scale
4: hydrogenchloride / ethanol; water / 8 h / 50 - 55 °C / Industrial scale
5: cerium(III) chloride heptahydrate; sodium tetrahydroborate / ethanol / 17 h / 10 °C / Industrial scale
6: pyridine / acetonitrile / 23 h / 10 - 20 °C / Industrial scale
7: sodium tert-pentoxide / toluene / 12 h / 35 - 85 °C / Industrial scale
8: acetic acid / water / 130 °C
9: triethylamine; lithium chloride; pivaloyl chloride / tetrahydrofuran / 8 h / 25 °C / Industrial scale
10: tetrahydrofuran / -20 °C / Industrial scale
11: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 25 °C / Industrial scale
12: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-methyl-1H-imidazole / acetonitrile / 3 h / 20 °C / Industrial scale
With pyridine; 1-methyl-1H-imidazole; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; thionyl chloride; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; pivaloyl chloride; sodium tert-pentoxide; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; acetic acid; triethylamine; lithium chloride; lithium hydroxide; In tetrahydrofuran; ethanol; tert-butyl methyl ether; water; toluene; acetonitrile;
Multi-step reaction with 7 steps
1: caesium carbonate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride / 1,4-dioxane; water / 100 °C
2: palladium on activated charcoal; hydrogen
3: lithium hydroxide / water; ethanol / 50 °C
4: triethylamine; pivaloyl chloride / tetrahydrofuran / 50 °C
5: sodium hexamethyldisilazane / tetrahydrofuran / -50 °C
6: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 °C
7: pyridine / ethyl acetate
With pyridine; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; palladium on activated charcoal; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; pivaloyl chloride; caesium carbonate; triethylamine; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; water; ethyl acetate;

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