N-(3-amino-3-oxo-propyl)-4-[(1S)-3-oxocyclopentyl]benzamide → N-(3-amino-3-oxo-propyl)-4-[(1S,3R/S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]cyclopentyl]benzamide

HRID 1614880Notes

Reaction equation

HRID 1614880 reaction equation
[NH2:1][C:2](=[O:20])[CH2:3][CH2:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:17][CH2:16][C:15](=O)[CH2:14]2)=[CH:9][CH:8]=1.Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C@H:29]([NH2:31])[CH3:30])=[CH:25][C:24]=1[O:32][CH3:33]>>[NH2:1][C:2](=[O:20])[CH2:3][CH2:4][NH:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:17][CH2:16][CH:15]([NH:31][C@@H:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[C:24]([O:32][CH3:33])[CH:25]=3)[CH3:30])[CH2:14]2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 49834310N-(3-amino-3-oxo-propyl)-4-[(1S)-3-oxocyclopentyl]benzamideHCID 53484667(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride

Product 1

HCID 68748026N-(3-amino-3-oxo-propyl)-4-[(1S,3R/S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]cyclopentyl]benzamide

Procedure

General procedure B was followed using N-(3-amino-3-oxo-propyl)-4-[(1S)-3-oxocyclopentyl]benzamide as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)-ethylamine hydrochloride as the amine. 1H NMR (600 MHz, DMSO) δ 8.39 (t, J=5.6 Hz, 1H), 7.74 (d, J=8.3 Hz, 2H), 7.37-7.31 (m, 3H), 7.16 (dd, J=8.6, 1.8 Hz, 1H), 7.10 (dd, J=11.5, 8.2 Hz, 1H), 6.91-6.87 (m, 1H), 6.82 (br s, 1H), 3.83 (s, 3H), 3.77-3.71 (m, 1H), 3.46-3.37 (m, 2H), 2.99-2.87 (m, 2H), 2.34 (t, J=7.3 Hz, 2H), 2.26-2.19 (m, 1H), 1.96-1.85 (m, 1H), 1.78-1.58 (m, 2H), 1.53-1.34 (m, 2H), 1.23 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-86d0281c21bf4ab2ad0b747495226cb4
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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