Dihydro-3(2H)-thiophenone → N-(2-oxo-2-{[(3R)-1-(tetrahydro-3-thienyl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

HRID 562583Notes

Reaction equation

HRID 562583 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][CH:35]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][CH2:21]N(C(OCC3C=CC=CC=3)=O)[CH2:19]2)[CH2:14]1)=[O:11])=[O:7].[S:38]1CCC(=O)C1.O=C1CCN(C(OCC2C=CC=CC=2)=O)C1>>[O:11]=[C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][CH2:21][S:38][CH2:19]2)[CH2:14]1)[CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:33]=[CH:34][CH:35]=[C:3]([C:2]([F:37])([F:36])[F:1])[CH:4]=1

Participants

4

Reactant 3

HCID 61252Dihydro-3(2H)-thiophenoneHCID 5612031-N-Cbz-3-pyrrolidinoneHCID 16061463benzyl (3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3'-bipyrrolidine-1'-carboxylate

Product 1

HCID 16666600N-(2-oxo-2-{[(3R)-1-(tetrahydro-3-thienyl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

Procedure

The title compound was synthesized in similar fashion to benzyl (3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3′-bipyrrolidine-1′-carboxylate, whereby dihydrothiophen-3(2H)-one was substituted for benzyl 3-oxopyrrolidine-1-carboxylate, and was isolated, as a mixture of diastereomers, as a white solid. 1H-NMR (CDCl3) δ: 1.55-1.66 (m, 1H), 1.71-1.81 (m, 1H), 2.03-2.14 (m, 1H), 2.15-2.26 (m, 1H), 2.33-2.39 (m, 1H), 2.52-2.58 (m, 1H), 2.63-2.73 (m, 3H), 2.74-2.81 (m, 4H), 4.07 (d, J=4.8 Hz, 2H), 4.36-4.38 (m, 1H), 7.04 (d, J=7.8 Hz, 1H), 7.46 (t, J=7.9 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.81 (t, J=4.9 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 8.03 (s, 1H). MS m/z: 402 (M+1)

Workup

  1. customwas isolated, as a mixture of diastereomers, as a white solid

Sources & evidence

ORD record
ord-ae80e17ead1c46259172ba37b3375a8c
Source dataset
uspto-grants-2011_11
Patent number
US08067415B2

Reaction notes

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