4-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1) → HCID 178425798, compound
Reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]1[NH:15][C:14]([C:16]2([CH3:20])[CH2:19][O:18][CH2:17]2)=[N:13][C:12]=1[CH3:21].CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.[NH:40]1[CH2:45][CH2:44][CH:43]([C:46]2[CH:53]=[CH:52][C:49]([C:50]#[N:51])=[CH:48][CH:47]=2)[CH2:42][CH2:41]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[CH:53]=[CH:52][C:49]([C:50]#[N:51])=[CH:48][CH:47]=3)[CH2:42][CH2:41]2)=[O:8])=[CH:4][C:3]=1[C:11]1[NH:15][C:14]([C:16]2([CH3:20])[CH2:19][O:18][CH2:17]2)=[N:13][C:12]=1[CH3:21]Participants
Procedure
The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 4-methyl-3-(4-methyl-2-(3-methyloxetan-3-yl)-1H-imidazol-5-yl)benzoic acid (compound 177.2) was used in place of 3-(2,4-dimethyl-1H-imidazol-5-yl)-4-methylbenzoic acid (compound 5.7) and 4-(piperidin-4-yl)benzonitrile hydrochloride (compound 1.2) was used in place of 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2). m/z (ES+) 455 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 11.78 (br, 1H), 7.78 (d, J=8.0 Hz, 2H), 7.53 (d, J=8.0 Hz, 2H), 7.40-7.23 (m, 3H), 4.92 (t, J=6.0 Hz, 5.2 Hz, 2H), 4.78-4.52 (m, 1H), 4.43 (t, J=5.2 Hz, 4.8 Hz, 2H), 3.91-3.71 (m, 1H), 3.24-3.08 (m, 1H), 2.98-2.88 (m, 2H), 2.34 and 2.25 (2 singlets, CH3, 3H), 2.16 and 2.03 (2 singlets, amide rotamers, CH3, 3H), 1.91-1.59 (m, 4H), 1.69 and 1.68 (2 singlets, CH3, 3H).
Sources & evidence
- ORD record
- ord-221fa41d44844042ae838fb748a4c5d0
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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