4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178424668, compound

HRID 1488016Notes

Reaction equation

HRID 1488016 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]([C:10]3[C:11]([CH3:20])=[CH:12][C:13]([CH3:19])=[C:14]([CH:18]=3)[C:15]([OH:17])=O)=[C:7]([CH3:9])[N:8]=2)[CH2:3][CH2:2]1.CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.[F:39][C:40]1([C:44]2[CH:51]=[CH:50][C:47]([C:48]#[N:49])=[CH:46][CH:45]=2)[CH2:43][NH:42][CH2:41]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[CH:1]1([C:4]2[NH:5][C:6]([C:10]3[C:11]([CH3:20])=[CH:12][C:13]([CH3:19])=[C:14]([CH:18]=3)[C:15]([N:42]3[CH2:41][C:40]([C:44]4[CH:45]=[CH:46][C:47]([C:48]#[N:49])=[CH:50][CH:51]=4)([F:39])[CH2:43]3)=[O:17])=[C:7]([CH3:9])[N:8]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochlorideHCID 900213344-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride2×HCID 178424669HCID 178424669, compound2×HCID 178432711HCID 178432711, compound

Product 1

HCID 178424668HCID 178424668, compound

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5, except 5-(2-cyclopropyl-4-methyl-1H-imidazol-5-yl)-2,4-dimethylbenzoic acid (compound 160.4) 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+) 429 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 11.52 (br, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.76 (dd, J=8.4 Hz, 3.2 Hz, 2H), 7.21 (d, J=6.8 Hz, 1H), 7.13 (s, 1H), 4.56-4.34 (m, 4H), 2.35 and 2.32 (2 singlets, CH3, 3H), 2.43 and 2.18 (2 singlets, CH3, 3H), 2.07 and 1.93 (2 singlets, CH3, 3H), 1.90-1.80 (m, 1H), 0.88-0.74 (m, 4H).

Sources & evidence

ORD record
ord-2c423e2c516d421da0a26f831bb274ec
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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