(3s)-3-[4-(Morpholine-4-carbonyl)phenyl]-cyclopentanone → [4-[(1S,3R/S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]-cyclopentyl]phenyl]-morpholino-methanone

HRID 1614877Notes

Reaction equation

HRID 1614877 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:19][CH2:18][C:17](=O)[CH2:16]3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]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]>>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C@H:29]([NH:31][CH:17]2[CH2:18][CH2:19][C@H:15]([C:12]3[CH:13]=[CH:14][C:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])=[CH:10][CH:11]=3)[CH2:16]2)[CH3:30])=[CH:25][C:24]=1[O:32][CH3:33]

Participants

3

Reactant 2

HCID 49833947(3s)-3-[4-(Morpholine-4-carbonyl)phenyl]-cyclopentanoneHCID 53484667(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride

Product 1

HCID 69901892[4-[(1S,3R/S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]-cyclopentyl]phenyl]-morpholino-methanone

Procedure

General procedure B was followed using (3S)-3-[4-(Morpholine-4-carbonyl)phenyl]-cyclopentanone (preparation 15) as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. 1H NMR (600 MHz, DMSO) δ 7.30-7.27 (m, 2H), 7.23 (d, J=8.2 Hz, 2H), 7.16 (dd, J=8.6, 1.9 Hz, 1H), 7.10 (dd, J=11.5, 8.2 Hz, 1H), 6.89 (ddd, J=8.1, 4.4, 1.9 Hz, 1H), 3.82 (s, 3H), 3.73 (q, J=6.4 Hz, 1H), 3.57 (m, 4H), 3.32 (m, 4H), 3.27-3.19 (m, 1H), 3.06-3.00 (m, 1H), 2.11-1.90 (m, 2H), 1.78-1.72 (m, 1H), 1.65-1.57 (m, 1H), 1.53-1.41 (m, 2H), 1.24 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-8232a6a0e6be4610bbbda3d2c1c61407
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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