Benzamide → N-(2-oxo-2-{[(3S)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

HRID 564388Notes

Reaction equation

HRID 564388 reaction equation
[O:1]=[C:2]([NH:17][C@@H:18]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:19]1)[CH2:3][NH:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.C(N)(=O)C1C=CC=CC=1.O=C(N[C@@H]1CCNC1)CNC(=O)C1C=CC=C(C(F)(F)F)C=1>>[O:1]=[C:2]([NH:17][C@H:18]1[CH2:22][CH2:21][N:20]([CH:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH2:19]1)[CH2:3][NH:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1

Participants

4

Reactant 3

HCID 2331BenzamideHCID 57814132N-(2-oxo-2-{[(3R)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamideHCID 59556069(R)-N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 57814129N-(2-oxo-2-{[(3S)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide

Procedure

The title compound was synthesized in a similar fashion to N-(2-oxo-2-{[(3R)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}ethyl)-3-(trifluoromethyl)benzamide, substituting (S)—N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-trifluoromethyl)benzamide for (R)—N-(2-oxo-2-(pyrrolidin-3-ylamino)ethyl)-3-(trifluoromethyl)benzamide 1H-NMR (CD3OD) δ: 1.69-1.77 (m, 2H), 2.01-2.09 (m, 3H), 2.39-2.46 (m, 1H), 3.24-3.44 (in 5H), 3.51-3.59 (m, 2H), 3.96-4.09 (m, 4H), 4.50-4.53 (m, 1H), 7.70 (t, J=7.9 Hz, 1H), 7.87 (d, J=7.5 Hz, 1H), 8.15 (d, J=8.4 Hz, 1H), 8.21 (s, 1H), 8.34 (s, 1H). MS m/z: 400 (M+1).

Sources & evidence

ORD record
ord-9636b868f8e34539a8b0f4fbcdb8dcee
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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