4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178494306, compound

HRID 1487989Notes

Reaction equation

HRID 1487989 reaction equation
[CH:1]1([C:4]2[C:12]([C:13]3[NH:17][C:16]([O:18][CH3:19])=[N:15][N:14]=3)=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([CH3:20])[CH:5]=2)[CH2:3][CH2:2]1.Cl.[F:22][C:23]1([C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)[CH2:26][NH:25][CH2:24]1.CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[CH:1]1([C:4]2[C:12]([C:13]3[NH:17][C:16]([O:18][CH3:19])=[N:15][N:14]=3)=[CH:11][C:7]([C:8]([N:25]3[CH2:24][C:23]([C:27]4[CH:28]=[CH:29][C:30]([C:31]#[N:32])=[CH:33][CH:34]=4)([F:22])[CH2:26]3)=[O:10])=[C:6]([CH3:20])[CH:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochloride2×HCID 900213344-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride2×HCID 178432711HCID 178432711, compound2×HCID 1784943084-Cyclopropyl-5-(5-methoxy-1H-1,2,4-triazol-3-yl)-2-methylbenzoic acid2×

Product 1

HCID 178494306HCID 178494306, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 4-cyclopropyl-5-(5-methoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzoic acid (compound 91.6) and 4-(3-fluoroazetidin-3-yl)benzonitrile (compound 43.4) were used in place of 3-(2,4-dimethyl-1H-imidazol-5-yl)-4-methylbenzoic acid (compound 5.7) and 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2), respectively. m/z (ES+) 432 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 13.66-13.01 (br, 1H), 7.96 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.0 Hz, 2H), 7.61 (s, 1H), 6.86 (s, 1H), 4.60-4.38 (m, 4H), 3.91 (s, 3H), 2.82 (m, 1H), 2.34 (s, 3H), 0.94 (m, 2H), 0.71 (m, 2H).

Sources & evidence

ORD record
ord-af0904eccf644e538059641b0f9a3ff6
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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