4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178424671, compound
Reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([C:12]2[NH:16][C:15]([C:17]3([CH3:21])[CH2:20][O:19][CH2:18]3)=[N:14][C:13]=2[CH3:22])=[CH:7][C:3]=1[C:4](O)=[O:5].CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.[F:41][C:42]1([C:46]2[CH:53]=[CH:52][C:49]([C:50]#[N:51])=[CH:48][CH:47]=2)[CH2:45][NH:44][CH2:43]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]([C:17]3([CH3:21])[CH2:20][O:19][CH2:18]3)=[N:14][C:13]=2[CH3:22])=[CH:7][C:3]=1[C:4]([N:44]1[CH2:43][C:42]([C:46]2[CH:47]=[CH:48][C:49]([C:50]#[N:51])=[CH:52][CH:53]=2)([F:41])[CH2:45]1)=[O:5]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-(3-methyloxetan-3-yl)-1H-imidazol-5-yl)benzoic acid (compound 175.4) 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+) 459 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 11.73 (br, 1H), 7.95 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.25 and 7.24 (2 singlets, Ar—H, 1H), 7.19 and 7.16 (2 singlets, Ar—H, 1H), 4.94-4.86 (m, 2H), 4.57-4.35 (m, 6H), 2.36 and 2.34 (2 singlets, CH3, 3H), 2.29 and 2.19 (2 singlets, CH3, 3H), 2.14 and 2.00 (2 singlets, CH1, 3H), 1.67 (s, 3H).
Sources & evidence
- ORD record
- ord-24985b6f4a4144deba3bc83445949c64
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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