6-Chlorobenzo[b]thiophene-2-sulfonyl chloride → 6-Chlorobenzo[b]thiophene-2-sulfonic acid [1-(5-cyano-2-hydroxy-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

HRID 2777Notes

Reaction equation

HRID 2777 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=2[OH:17])[C:12]#[N:13])[C:4]1=[O:18].[Cl:19][C:20]1[CH:21]=[CH:22][C:23]2[CH:27]=[C:26]([S:28](Cl)(=[O:30])=[O:29])[S:25][C:24]=2[CH:32]=1>>[C:12]([C:11]1[CH:14]=[CH:15][C:16]([OH:17])=[C:9]([CH:10]=1)[CH2:8][N:5]1[CH2:6][CH2:7][C@H:3]([NH:2][S:28]([C:26]2[S:25][C:24]3[CH:32]=[C:20]([Cl:19])[CH:21]=[CH:22][C:23]=3[CH:27]=2)(=[O:30])=[O:29])[C:4]1=[O:18])#[N:13]

Participants

3

Reactant 2

HCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 193509103-[(3-Amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride

Product 1

HCID 545212976-Chlorobenzo[b]thiophene-2-sulfonic acid [1-(5-cyano-2-hydroxy-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Procedure

The title compound is prepared from 3-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride as described in EXAMPLE 17, Part G substituting 6-chlorobenzo[b]thiophene-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with Et2O to give the title compound as a white solid.

Workup

  1. customThe crude product is triturated with Et2O

Sources & evidence

ORD record
ord-5319433aef944914adab5a67046697cc
Source dataset
uspto-grants-1998_03
Patent number
US05731315

Reaction notes

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