4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178425810, compound

HRID 1487918Notes

Reaction equation

HRID 1487918 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[CH3:17])[C:11]([OH:13])=O)[NH:4][N:3]=1.Cl.[F:19][C:20]1([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=2)[CH2:23][NH:22][CH2:21]1.CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[CH3:17])[C:11]([N:22]2[CH2:21][C:20]([C:24]3[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=3)([F:19])[CH2:23]2)=[O:13])[NH:4][N:3]=1

Participants

5

Reactant 4

HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochloride2×HCID 900213344-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride2×HCID 178425892HCID 178425892, compound2×HCID 178432711HCID 178432711, compound2×

Product 1

HCID 178425810HCID 178425810, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 3-(3,4-dimethyl-1H-pyrazol-5-yl)-4-methylbenzoic acid (compound 59.3) 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+) 389 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.45-12.26 (br, 1H), 7.95 (d, J=8.0 Hz, 2H), 7.79 (d, J=8.0 Hz, 2H), 7.65 (d, J=7.2 Hz, 1H), 7.52 (d, J=2.0 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 4.98-4.42 (m, 4H), 2.25 (s, 3H), 2.17 (s, 3H), 1.83 (s, 3H).

Sources & evidence

ORD record
ord-f459bf14337642a28ca57d15b665a8bf
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

Loading…