5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → 5-Chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [1-(2-cyanopyridin-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide

HRID 619859Notes

Reaction equation

HRID 619859 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[C:10]1=[O:23].[Cl:24][C:25]1[CH:38]=[CH:37][C:28]2[S:29][C:30]([S:33](Cl)(=[O:35])=[O:34])=[C:31]([CH3:32])[C:27]=2[CH:26]=1>>[C:21]([C:17]1[CH:16]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][C@H:9]([NH:8][S:33]([C:30]3[S:29][C:28]4[CH:37]=[CH:38][C:25]([Cl:24])=[CH:26][C:27]=4[C:31]=3[CH3:32])(=[O:35])=[O:34])[C:10]2=[O:23])[CH:20]=[CH:19][N:18]=1)#[N:22]

Participants

3

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 183924424-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)pyridine-2-carbonitrile trifluoroacetate

Product 1

HCID 544718725-Chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [1-(2-cyanopyridin-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide

Procedure

The title compound is prepared as described in EXAMPLE 125, Part C using 4-(3-(S)-amino-2-oxopyrrolidin-1-ylmethyl)pyridine-2-carbonitrile trifluoroacetate in place of 4-(3-(S)-amino-2-oxopyrrolidine-1-ylmethyl)-thiophene-2-carbonitrile hydrochloride and with 5-chloro-3-methyl-benzo[b]thiophene-2-sulfonyl chloride in place of 7-methoxynaphthalene-2-sulfonyl chloride. The crude product is purified by column chromatography eluting with gradient of 25% EtOAc/CH2Cl2 to 50% EtOAc/CH2Cl2 to afford the title compound as a white solid.

Workup

  1. customThe title compound is prepared
  2. customThe crude product is purified by column chromatography
  3. washeluting with gradient of 25% EtOAc/CH2Cl2 to 50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-1ff99d9ea43d4d5f8a6061d71411b051
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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