4-(Azetidin-3-yl)benzonitrile hydrochloride → Methyl 4-(5-(5-(3-(4-cyanophenyl)-3-fluoroazetidine-1-carbonyl)-2-methylphenyl)-4-methyl-1H-imidazol-2-yl)-4-methylpiperidine-1-carboxylate
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:12][N:11]([C:13]([C:15]3[CH:16]=[CH:17][C:18]([CH3:41])=[C:19]([C:21]4[NH:25][C:24]([C:26]5([CH3:39])[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35](C)(C)C)=[O:33])[CH2:28][CH2:27]5)=[N:23][C:22]=4[CH3:40])[CH:20]=3)=[O:14])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(C1C=CC(C2CN(C(C3C=CC(C)=C(C4N=C(C5CCN(C(OC(C)(C)C)=O)CC5)NC=4C)C=3)=O)C2)=CC=1)#N.Cl.[F:83]C1(C2C=CC(C#N)=CC=2)CNC1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([F:83])[CH2:12][N:11]([C:13]([C:15]3[CH:16]=[CH:17][C:18]([CH3:41])=[C:19]([C:21]4[NH:25][C:24]([C:26]5([CH3:39])[CH2:31][CH2:30][N:29]([C:32]([O:34][CH3:35])=[O:33])[CH2:28][CH2:27]5)=[N:23][C:22]=4[CH3:40])[CH:20]=3)=[O:14])[CH2:10]2)=[CH:5][CH:4]=1)#[N:2]Participants
5
Reactant 4
Product 1
Procedure
The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 184, except tert-butyl 4-(5-(5-(3-(4-cyanophenyl)azetidine-1-carbonyl)-2-methylphenyl)-4-methyl-1H-imidazol-2-yl)-4-methylpiperidine-1-carboxylate (compound 185.3) was used in place of tert-butyl 4-(4-(5-(3-(4-cyanophenyl)azetidine-1-carbonyl)-2-methylphenyl)-5-methyl-1H-imidazol-2-yl)piperidine-1-carboxylate (compound 182.3) and 4-(3-fluoroazetidin-3-yl)benzonitrile hydrochloride (compound 43.4) was used in place of 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2). m/z (ES+) 530 (M+H)+.
Sources & evidence
- ORD record
- ord-71a9390b4e194b57b6aa970a195b62f8
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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