5-Chlorothieno[3,2-b]pyridine-2-sulfonyl chloride → 5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(2-amino-5-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

HRID 1636782Notes

Reaction equation

HRID 1636782 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[CH2:12][N:13]1[CH2:17][CH2:16][C@H:15]([NH2:18])[C:14]1=[O:19].[Cl:20][C:21]1[N:26]=[C:25]2[CH:27]=[C:28]([S:30](Cl)(=[O:32])=[O:31])[S:29][C:24]2=[CH:23][CH:22]=1>>[NH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[CH2:12][N:13]1[CH2:17][CH2:16][C@H:15]([NH:18][S:30]([C:28]2[S:29][C:24]3[C:25](=[N:26][C:21]([Cl:20])=[CH:22][CH:23]=3)[CH:27]=2)(=[O:31])=[O:32])[C:14]1=[O:19]

Participants

3

Reactant 2

HCID 220172995-Chlorothieno[3,2-b]pyridine-2-sulfonyl chlorideHCID 228836314-amino-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)benzonitrile dihydrochloride

Product 1

HCID 540563825-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(2-amino-5-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Procedure

The title compound is prepared from 4-amino-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile dihydrochloride as described in EXAMPLE 17, Part F using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/CH2Cl2 to 25% EtOAc/CH2 cl2 to afford a white solid.

Workup

  1. customThe crude product is purified by column chromatography
  2. washeluting with a gradient of 10% EtOAc/CH2Cl2 to 25% EtOAc/CH2 cl2
  3. customto afford a white solid

Sources & evidence

ORD record
ord-2d2d7f9e6ae54a2aacebddb2845c7724
Source dataset
uspto-grants-2000_03
Patent number
US06034093

Reaction notes

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