Reaction #1723966

ord-8f7b4ff3455f4a88bca280f54fd91cff

Reaction equation

O=S(=O)(Cl)c1cc2ccccc2s1
benzo[b]thiophene-2-sulfonyl chloride
Cl.N#Cc1cccc(CN2CC[C@H](N)C2=O)c1
3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride
CSc1nccc(-c2ccc(S(=O)(=O)Cl)s2)n1
5-[2-(methylthio)-pyrimidin-4-yl]thiophene-2-sulfonyl chloride
→
CSc1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1
title compound
CSc1nccc(-c2ccc(S(=O)(=O)N[C@H]3CCN(Cc4cccc(C#N)c4)C3=O)s2)n1
5-(2-Methylsulfanyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Reactants

O=S(=O)(Cl)c1cc2ccccc2s1
benzo[b]thiophene-2-sulfonyl chloride
Cl.N#Cc1cccc(CN2CC[C@H](N)C2=O)c1
3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride
CSc1nccc(-c2ccc(S(=O)(=O)Cl)s2)n1
5-[2-(methylthio)-pyrimidin-4-yl]thiophene-2-sulfonyl chloride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 5-[2-(methylthio)-pyrimidin-4-yl]thiophene-2-sulfonyl chloride in a place of benzo[b]thiophene-2-sulfonyl chloride. The crude product is obtained as a white solid and is of sufficient purity to be used in the subsequent step.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06034093uspto-grants-2000_03