4-(Azetidin-3-yl)benzonitrile hydrochloride → HCID 178425807, compound

HRID 1488039Notes

Reaction equation

HRID 1488039 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[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.[F:40][C:41]1([C:45]2[CH:52]=[CH:51][C:48]([C:49]#[N:50])=[CH:47][CH:46]=2)[CH2:44][NH:43][CH2:42]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[F:40][C:41]1([C:45]2[CH:46]=[CH:47][C:48]([C:49]#[N:50])=[CH:51][CH:52]=2)[CH2:42][N:43]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]3[NH:15][C:14]([C:16]4([CH3:20])[CH2:17][O:18][CH2:19]4)=[N:13][C:12]=3[CH3:21])[CH:4]=2)[CH2:44]1

Participants

5

Reactant 4

HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochlorideHCID 900213344-(3-Fluoroazetidin-3-yl)benzonitrile hydrochloride2×HCID 178425882HCID 178425882, compound2×HCID 178432711HCID 178432711, compound

Product 1

HCID 178425807HCID 178425807, 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-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-(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+) 445 (M+H)+. 1H NMR (400 MHz, DMSO-d6): δ 11.80 (br, 1H), 7.96 (dd, J=8.0 Hz, 2.4 Hz, 2H), 7.80 (d, J=8.4 Hz, 2H), 7.67-7.52 (m, 2H), 7.44-7.33 (m, 1H), 4.95-4.89 (m, 2H), 4.89-4.46 (m, 4H), 4.46-4.40 (m, 2H), 3.36 and 2.26 (2 singlets, CH3, 3H), 2.17 and 2.03 (2 singlets, CH3, 3H), 1.69 and 1.68 (2 singlets, CH3, 3H).

Sources & evidence

ORD record
ord-889a5af5b9df460a88bf820becc018cd
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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