Acetonitrile → 5-Pyridin-3-yl-thiophene-2-sulfonic acid [1-(2-amino-5-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:11][C:10]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:8]=2)[CH:2]=1.Cl.[NH2:17][C@H:18]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])[C:19]1=[O:32].CC#[N:35]>>[NH2:35][C:31]1[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=1[CH2:23][N:20]1[CH2:21][CH2:22][C@H:18]([NH:17][S:12]([C:10]2[S:11][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:8][CH:9]=2)(=[O:14])=[O:13])[C:19]1=[O:32]

Participants

Reactant 3

HCID 6342Acetonitrile

HCID 106589765-Pyridin-3-yl-thiophene-2-sulfonyl chloride

HCID 228707863-(3-(S)-Amino-2-oxopyrrolidin-1-ylmethyl)benzonitrile hydrochloride

Product 1

HCID 536889905-Pyridin-3-yl-thiophene-2-sulfonic acid [1-(2-amino-5-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide

Procedure

The title compound is prepared in CH3CN instead of CH2Cl2 as described in EXAMPLE 1, Part E using 5-pyridin-3-yl-thiophene-2-sulfonyl choride in place of benzo[b]thiophene-2-sulfonyl chloride and substituting 4-amino-[3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)]-benzonitrile dihydrochloride for 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride. The crude product is obtained by diluting with ethyl acetate and washing with saturated sodium bicarbonate (aq), water and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with 50% EtOAc/CH2Cl2 to give a light brown solid.