4-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1) → 4-(1-(4-Cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoyl)-4-fluoropiperidin-4-yl)benzonitrile
Reaction equation
[CH:1]1([C:5]2[C:26]([C:27]3[NH:28][C:29]([CH2:32][O:33][CH3:34])=[CH:30][N:31]=3)=[CH:25][C:8]([C:9]([N:11]3[CH2:16][CH2:15][CH:14]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=4)[CH2:13][CH2:12]3)=[O:10])=[C:7]([CH3:35])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[F:37]C1(C2C=CC(C#N)=CC=2)CCNCC1.Cl.N1CCC(C2C=CC(C#N)=CC=2)CC1>>[CH:1]1([C:5]2[C:26]([C:27]3[NH:28][C:29]([CH2:32][O:33][CH3:34])=[CH:30][N:31]=3)=[CH:25][C:8]([C:9]([N:11]3[CH2:12][CH2:13][C:14]([C:17]4[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=4)([F:37])[CH2:15][CH2:16]3)=[O:10])=[C:7]([CH3:35])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared using standard chemical manipulations and procedures similar to those used for preparation of 4-(1-(4-cyclobutyl-5-(5-(methoxymethyl)-1H-imidazol-2-yl)-2-methylbenzoyl)piperidin-4-yl)benzonitrile (compound 246), using 4-(4-fluoropiperidin-4-yl)benzonitrile hydrochloride (compound 11.2 HCl salt) instead of 4-(piperidin-4-yl)benzonitrile hydrochloride (compound 1.5). m/z (ES+) 487 (M+H)+. 1H NMR (400 MHz, CD3OD): δ 7.79-7.67 (m, 2H), 7.66 (d, 3H), 7.53-7.39 (m, 2H), 4.99-4.93 (m, 1H), 4.85 (s, 2H), 3.76-3.56 (m, 3H), 3.50 (s, 3H), 2.42 and 2.34 (2 singlets, amide rotamers, ArCH3, 3H), 2.27-1.97 (m, 8H), 1.92-1.81 (m, 2H), 1.35-1.26 (m, 1H).
Sources & evidence
- ORD record
- ord-f1e8d516bc16483fb49c368141dab476
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871790B2
Reaction notes
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