(R)-4-(3-Oxocyclopentyl)benzonitrile → 4-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]cyclopentyl]benzonitrile

HRID 1614869Notes

Reaction equation

HRID 1614869 reaction equation
O=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH2:3]1.Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH2:25])[CH3:24])=[CH:19][C:18]=1[O:26][CH3:27]>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]([NH:25][C@H:2]2[CH2:6][CH2:5][C@@H:4]([C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=3)[CH2:3]2)[CH3:24])=[CH:19][C:18]=1[O:26][CH3:27]

Participants

3

Reactant 2

HCID 49834135(R)-4-(3-Oxocyclopentyl)benzonitrileHCID 53484667(R)-1-(4-Fluoro-3-methoxyphenyl)ethanamine hydrochloride

Product 1

HCID 687501784-[(1R,3S)-3-[[(1R)-1-(4-fluoro-3-methoxy-phenyl)ethyl]amino]cyclopentyl]benzonitrile

Procedure

General procedure B was followed using 4-[(1R)-3-oxocyclopentyl]benzonitrile as the ketone and (1R)-1-(4-fluoro-3-methoxyphenyl)ethylamine hydrochloride as the amine. 1H NMR (300 MHz, DMSO) δ 7.76-7.69 (m, 2H), 7.44 (d, J=8.3 Hz, 2H), 7.15 (dd, J=8.6, 1.9 Hz, 1H), 7.09 (dd, J=11.5, 8.3 Hz, 1H), 6.88 (ddd, J=8.2, 4.5, 1.9 Hz, 1H), 3.82 (s, 3H), 3.75 (d, J=6.2 Hz, 1H), 3.07-2.85 (m, 2H), 2.23-2.03 (m, 2H), 2.00-1.54 (m, 3H), 1.40-1.19 (m, 1H), 1.23 (d, J=6.6 Hz, 3H).

Sources & evidence

ORD record
ord-73fa3b5f052f4494b8a290d8c8d5b423
Source dataset
uspto-grants-2014_07
Patent number
US08765676B2

Reaction notes

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