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

HRID 1614878Notes

Reaction equation

HRID 1614878 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.[O:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[C:30]([C@H:31]([NH2:33])[CH3:32])[C:25]=2[O:24][CH2:23]1>>[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:30]3[C:25]4[O:24][CH2:23][O:22][C:26]=4[CH:27]=[CH:28][CH:29]=3)[CH3:32])[CH2:14]2)=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 49834310N-(3-amino-3-oxo-propyl)-4-[(1S)-3-oxocyclopentyl]benzamideHCID 68754023(1R)-1-(1,3-dioxaindan-4-yl)ethan-1-amine hydrochloride

Product 1

HCID 68748899N-(3-amino-3-oxo-propyl)-4-[(1S,3R/S)-3-[[(1R)-1-(1,3-benzodioxol-4-yl)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-(1,3-benzodioxol-4-yl)ethanamine hydrochloride as the amine. 1H NMR (600 MHz, DMSO) δ 8.39 (t, 1H), 7.74 (d, J=8.2 Hz, 2H), 7.36-7.31 (m, 3H), 6.92 (d, J=7.8 Hz, 1H), 6.84-6.79 (m, 2H), 6.78-6.75 (m, 1H), 5.97 (s, 2H), 3.91 (q, J=6.7 Hz, 1H), 3.46-3.31 (m, 2H), 3.01-2.93 (m, 2H), 2.33 (t, 2H), 2.24-2.17 (m, 1H), 1.96-1.86 (m, 1H), 1.80-1.59 (m, 2H), 1.54-1.46 (m, 1H), 1.42-1.34 (m, 1H), 1.26 (d, J=6.7 Hz, 3H).

Sources & evidence

ORD record
ord-7d2ccfd306354beeb4ff099ee53d09a1
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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