3-(Bromomethyl)thiophene → 7-methoxy-naphthalene-2-sulfonic acid-[1-(2-cyanothiophene-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]thiophene-3-ylmethylamide

HRID 619864Notes

Reaction equation

HRID 619864 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][S:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=4)[CH:19]=3)(=[O:17])=[O:16])[C:10]2=[O:30])[CH:7]=1)#[N:2].Br[CH2:32][C:33]1[CH:37]=[CH:36][S:35][CH:34]=1>>[C:1]([C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][C@H:11]([N:14]([CH2:32][C:33]3[CH:37]=[CH:36][S:35][CH:34]=3)[S:15]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=4)[CH:19]=3)(=[O:17])=[O:16])[C:10]2=[O:30])[CH:7]=1)#[N:2]

Participants

3

Reactant 2

HCID 5207033-(Bromomethyl)thiopheneHCID 10670821HCID 10670821, compound

Product 1

HCID 183924517-methoxy-naphthalene-2-sulfonic acid-[1-(2-cyanothiophene-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]thiophene-3-ylmethylamide

Procedure

The title compound is prepared from 7-methoxynaphthalene-2-sulfonic acid [1-(2-cyanothiophen-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]amide (0.5 g, 1.16 mmol) as described in EXAMPLE 126, Part A, using 3-bromomethylthiophene in place of methyl iodide. The crude product is purified by column chromatography eluting with 60% EtOAc/hexanes to afford 7-methoxy-naphthalene-2-sulfonic acid-[1-(2-cyanothiophene-4-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]thiophene-3-ylmethylamide as a white solid (0.18 g, 0.33 mmol).

Workup

  1. customThe crude product is purified by column chromatography
  2. washeluting with 60% EtOAc/hexanes

Sources & evidence

ORD record
ord-576cd37cedc94e4f8cdf5d8c0616ada5
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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