Benzyl Bromide → 5-Chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-benzylamide

HRID 619842Notes

Reaction equation

HRID 619842 reaction equation
[C:1]([C:3]1[S:7][CH:6]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][S:15]([C:18]3[S:22][C:21]4[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=4[C:19]=3[CH3:28])(=[O:17])=[O:16])[C:10]2=[O:29])[CH:4]=1)#[N:2].C(C1SC=C(CN2CC[C@H](NS([C:47]3[CH:56]=[CH:55][C:54]4[C:49](=[CH:50]C(OC)=CC=4)[CH:48]=3)(=O)=O)C2=O)C=1)#N.C(Br)C1C=CC=CC=1>>[C:1]([C:3]1[S:7][CH:6]=[C:5]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([N:14]([CH2:50][C:49]3[CH:54]=[CH:55][CH:56]=[CH:47][CH:48]=3)[S:15]([C:18]3[S:22][C:21]4[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=4[C:19]=3[CH3:28])(=[O:17])=[O:16])[C:10]2=[O:29])[CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 10670821HCID 10670821, compoundHCID 183924465-chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide

Product 1

HCID 572292915-Chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-benzylamide

Procedure

The title compound is prepared as in EXAMPLE 126, Part A using 5-chloro-3-methylbenzo[b]thiophene-2-sulfonic acid [1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide, prepared as in EXAMPLE 129, Part A, in place of 7-methoxynaphthalene-2-sulfonic acid [1-(5-cyanothiophen-3-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide and benzyl bromide in place of MeI. The crude product is purified by column chromatography eluting with gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes to afford the title compound as a white solid.

Workup

  1. customThe title compound is prepared as in EXAMPLE 126, Part A
  2. customThe crude product is purified by column chromatography
  3. washeluting with gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-e7ca366c9efb45b589c47438b9874526
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

Loading…