Sodium hydrosulfide → HCID 178461850, compound

HRID 869473Notes

Reaction equation

HRID 869473 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C@H:12]([C:14]2[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16](=[O:28])[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])[CH3:13])[CH:5]=[CH:4][N:3]=1.[SH-:35].[Na+]>CO>[SH:35][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][C@H:12]([C:14]2[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:16](=[O:28])[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][C:18]=3[C:24]([F:27])([F:26])[F:25])[CH3:13])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 86676288(S)-3-(1-(2-chloro-3-nitropyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one

Product 1

HCID 178461850HCID 178461850, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-3-(1-(2-chloro-3-nitropyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl) isoquinolin-1 (2H)-one III-33 (500 mg, 1.0 mmol, 1 eq) in MeOH (10 mL), sodium hydrosulphide (69 g, 1.29 mmol, 1.2 eq) was added and the resulting mixture was stirred at reflux for 2 h. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2-3% MeOH-DCM) to afford the product, (S)-3-(1-(2-mercapto-3-nitropyridin-4-ylamino) ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one III-34.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (2-3% MeOH-DCM)

Sources & evidence

ORD record
ord-f6429f33a4cf40398614b1c32f9ef723
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

Loading…