(R)-1-(3-Ethoxyphenyl)ethanamine hydrochloride → N-(3-amino-3-oxo-propyl)-4-[(1S,3R/S)-3-[[(1R)-1-(3-ethoxyphenyl)ethyl]-amino]cyclopentyl]benzamide

HRID 1614879Notes

Reaction equation

HRID 1614879 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.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([C@H:31]([NH2:33])[CH3:32])[CH:28]=[CH:29][CH:30]=1)[CH3:23]>>[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:33][C@@H:31]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH2:22][CH3:23])[CH:26]=3)[CH3:32])[CH2:14]2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 44828801(R)-1-(3-Ethoxyphenyl)ethanamine hydrochlorideHCID 49834310N-(3-amino-3-oxo-propyl)-4-[(1S)-3-oxocyclopentyl]benzamide

Product 1

HCID 68748904N-(3-amino-3-oxo-propyl)-4-[(1S,3R/S)-3-[[(1R)-1-(3-ethoxyphenyl)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-(3-ethoxyphenyl)-ethanamine hydrochloride as the amine. 1H NMR (600 MHz, DMSO) δ 8.37 (t, J=5.6 Hz, 1H), 7.70 (d, J=8.3 Hz, 2H), 7.33 (br s, 1H), 7.23 (d, J=8.3 Hz, 2H), 7.19 (t, J=7.8 Hz, 1H), 6.92 (s, 1H), 6.89 (d, J=7.6 Hz, 1H), 6.81 (br s, 1H), 6.74 (d, J=8.0 Hz, 1H), 4.00 (q, J=7.0 Hz, 2H), 3.75-3.66 (m, 1H), 3.28-3.20 (m, 1H), 3.08-3.00 (m, 1H), 2.58-2.52 (m, 2H), 2.32 (t, J=7.3 Hz, 2H), 2.12-1.41 (m, 7H), 1.31 (t, J=7.0 Hz, 3H), 1.23 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-545d4ad2f30e494e98c8dc5226ac79c3
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

Loading…