4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178494307, compound

HRID 1487983Notes

Reaction equation

HRID 1487983 reaction equation
[CH:1]1([C:5]2[C:13]([C:14]3[NH:18][C:17]([O:19][CH3:20])=[N:16][N:15]=3)=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([CH3:21])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.Cl.[F:23][C:24]1([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[CH2:27][NH:26][CH2:25]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:5]2[C:13]([C:14]3[NH:18][C:17]([O:19][CH3:20])=[N:16][N:15]=3)=[CH:12][C:8]([C:9]([N:26]3[CH2:25][C:24]([C:28]4[CH:29]=[CH:30][C:31]([C:32]#[N:33])=[CH:34][CH:35]=4)([F:23])[CH2:27]3)=[O:11])=[C:7]([CH3:21])[CH:6]=2)[CH2:2][CH2:3][CH2:4]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 178494309HCID 178494309, compound2×

Product 1

HCID 178494307HCID 178494307, 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-cyclobutyl-5-(5-methoxy-4H-1,2,4-triazol-3-yl)-2-methylbenzoic acid (compound 89.9) and 4-(3-fluoroazetidin-3-yl)benzonitrile hydrochloride (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+) 446 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 13.64-13.05 (br, 1H), 7.96 (d, J=8.0 Hz, 2H), 7.76 (d, J=8.0 Hz, 2H), 7.56 (s, 1H), 7.41 (s, 1H), 4.61-4.38 (m, 4H), 4.19 (m, 1H), 3.92 (s, 3H), 2.42 (s, 3H), 2.16 (m, 1H), 2.02 (m, 1H), 1.89 (m, 1H), 1.75 (m, 1H).

Sources & evidence

ORD record
ord-4d23b54a0d664c3f97df96e3e4229677
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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