4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178424677, compound
Reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[NH:16][C:15]([CH:17]3[CH2:20][O:19][CH2:18]3)=[N:14][C:13]=2[CH3:21])=[CH:7][C:3]=1[C:4]([OH:6])=O.CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.[F:40][C:41]1([C:45]2[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][CH:46]=2)[CH2:44][NH:43][CH2:42]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[NH:16][C:15]([CH:17]3[CH2:20][O:19][CH2:18]3)=[N:14][C:13]=2[CH3:21])=[CH:7][C:3]=1[C:4]([N:43]1[CH2:42][C:41]([C:45]2[CH:46]=[CH:47][C:48]([C:49]#[N:50])=[CH:51][CH:52]=2)([F:40])[CH2:44]1)=[O:6]Participants
Procedure
The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 2,4-dimethyl-5-(4-methyl-2-(oxetan-3-yl)-1H-imidazol-5-yl)benzoic acid (compound 180.4) was used in place of 3-(2,4-dimethyl-1H-imidazol-5-yl)-4-methylbenzoic acid (compound 5.7) 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+) 445 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 11.80 (br, 1H), 7.96 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.0 Hz, 2H), 7.24 (s, 1H), 7.18 (d, J=7.2 Hz, 2H), 4.87-4.75 (m, 4H), 4.60-4.36 (m, 4H), 4.31-4.21 (m, 1H), 2.35 (s, CH3, 3H), 2.90 and 2.20 (2 singlets, CH3, 3H), 2.13 and 2.02 (2 singlets, CH3, 3H).
Sources & evidence
- ORD record
- ord-6d81d77fc67649daad818251725e4659
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
Loading…