4-Chlorobenzenesulfonyl chloride → HCID 49787506, compound

HRID 1020003Notes

Reaction equation

HRID 1020003 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]2)=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>ClCCl>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([S:39]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])[CH2:9]3)=[C:4]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[CH:3]=2)(=[O:41])=[O:40])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 86664382HCID 86664382, compound

Product 1

HCID 49787506HCID 49787506, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[7-amino-5-(2-chloro-phenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoro-ethanone (80 mgs, 0.2 mmoles) was stirred in dichloromethane (12 mls) and triethylamine (80 ul, 0.58 mmoles) was added, followed by 4-chlorobenzenesulphonyl chloride (75 mgs, 0.36 mmoles). The reaction was flushed with nitrogen and left stirring at room temperature overnight. The reaction was purified by semi-preparative C18 HPLC (47 mgs, 44% yield, 100% pure, CO-AAW00034).

Workup

  1. customThe reaction was flushed with nitrogen
  2. waitleft
  3. customThe reaction was purified by semi-preparative C18 HPLC (47 mgs, 44% yield, 100% pure, CO-AAW00034)

Sources & evidence

ORD record
ord-d73e671965e5412396e866068bbcc6eb
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

Loading…