BMS-986205

Base Information

• Chemical Name: BMS-986205
• CAS No.: 1923833-60-6
• Molecular Formula: C₂₄H₂₄ClFN₂O
• Molecular Weight: 410.919
• Mol file: 1923833-60-6.mol

Synonyms:

Chemical Property of BMS-986205

Chemical Property:

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

Purity/Quality:

98% min ^*data from raw suppliers

BMS-986205 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: BMS-986205, also known as Linrodostat, ONO-7701 and F001287, a potent and selective, orally active IDO1 inhibitor with potential immunomodulating and antineoplastic activities.
• Uses: BMS-986205 is a compound being studied for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders.

Technology Process of BMS-986205

There total 22 articles about BMS-986205 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide (1923833-60-6)

Guidance literature:

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;

Reference yield:

4-bromine-6-fluoroquinoline (661463-17-8) → (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide (1923833-60-6)

Guidance literature:

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;

DOI:10.1021/acs.oprd.9b00359

Reference yield:

(R)-3-((R)-2-((1s,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanoyl)-4-phenyloxazolidin-2-one → (R)-N-(4-chlorophenyl)-2-((1S,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide (1923833-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 - 20 °C

2.1: propylphosphonic anhydride; pyridine / ethyl acetate / 0.08 h / 20 °C

2.2: 20 °C

With pyridine; propylphosphonic anhydride; dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; ethyl acetate;

upstream raw materials:

4-chloro-aniline

ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)acetate

ethyl 1,4-dioxaspiro[4,5]dec-8-ylideneacetate

ethyl 1,4-dioxaspiro[4.5]dec-8-ylacetate

Refernces

• 1、 -. "FORMULATED AND/OR CO-FORMULATED LIPOSOME COMPOSITIONS CONTAINING IDO ANTAGONIST PRODRUGS USEFUL IN THE TREATMENT OF CANCER AND METHODS THEREOF". Page/Page column 47. . Retrieved 2021/05/21.