4-(Azetidin-3-yl)benzonitrile hydrochloride → 4-(1-(3-(4-Chloro-1H-pyrazol-5-yl)-4-methylbenzoyl)-4-fluoropiperidin-4-yl)benzonitrile

HRID 1487914Notes

Reaction equation

HRID 1487914 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:10]([OH:12])=O.CC1NC(C2C=C(C=CC=2C)C(O)=O)=C(C)N=1.Cl.[F:35][C:36]1([C:42]2[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=2)[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.Cl.N1CC(C2C=CC(C#N)=CC=2)C1>>[Cl:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:10]([N:39]1[CH2:40][CH2:41][C:36]([C:42]2[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=2)([F:35])[CH2:37][CH2:38]1)=[O:12]

Participants

5

Reactant 4

HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochlorideHCID 682888554-(4-Fluoropiperidin-4-yl)benzonitrile hydrochloride2×HCID 900296813-(4-Chloro-1H-pyrazol-3-yl)-4-methylbenzoic acid2×HCID 178432711HCID 178432711, compound

Product 1

HCID 900331304-(1-(3-(4-Chloro-1H-pyrazol-5-yl)-4-methylbenzoyl)-4-fluoropiperidin-4-yl)benzonitrile

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for preparation of compound 5, except 3-(4-chloro-1H-pyrazol-5-yl)-4-methylbenzoic acid (compound 51.3) was used in place of 3-(2,4-dimethyl-1H-imidazol-5-yl)-4-methylbenzoic acid (compound 5.7) and 4-(4-fluoropiperidin-4-yl)benzonitrile hydrochloride (compound 13.4) was used in place of 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2). m/z (ES+) 423 (M+H)+.

Sources & evidence

ORD record
ord-38484350475c4eaf91113a472922835c
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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