4-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1) → 4-(1-(3-(2-(2-(Azetidin-1-yl)ethyl)-4-chloro-1H-imidazol-5-yl)-4-methylbenzoyl)azetidin-3-yl)benzonitrile

HRID 1488010Notes

Reaction equation

HRID 1488010 reaction equation
[N:1]1([CH2:5][CH2:6][C:7]2[NH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=O)=[C:10]([Cl:12])[N:11]=2)[CH2:4][CH2:3][CH2:2]1.ClC1N=C(COC)NC=1C1C=C(C=CC=1C)C(O)=O.Cl.[NH:43]1[CH2:46][CH:45]([C:47]2[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][CH:48]=2)[CH2:44]1.Cl.N1CCC(C2C=CC(C#N)=CC=2)CC1>>[N:1]1([CH2:5][CH2:6][C:7]2[NH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([N:43]3[CH2:46][CH:45]([C:47]4[CH:54]=[CH:53][C:50]([C:51]#[N:52])=[CH:49][CH:48]=4)[CH2:44]3)=[O:18])=[C:10]([Cl:12])[N:11]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 4

HCID 193916184-(Piperidin-4-yl)benzonitrile--hydrogen chloride (1/1)HCID 552549914-(Azetidin-3-yl)benzonitrile hydrochloride2×HCID 178425887HCID 178425887, compound2×HCID 178494679HCID 178494679, compound

Product 1

HCID 1784257944-(1-(3-(2-(2-(Azetidin-1-yl)ethyl)-4-chloro-1H-imidazol-5-yl)-4-methylbenzoyl)azetidin-3-yl)benzonitrile

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 27, except 3-(2-(2-(azetidin-1-yl)ethyl)-4-chloro-1H-imidazol-5-yl)-4-methylbenzoic acid (compound 157.3) was used in place of 3-(4-chloro-2-(methoxymethyl)-1H-imidazol-5-yl)-4-methylbenzoic acid (compound 27.5) and 4-(azetidin-3-yl)benzonitrile hydrochloride (compound 5.2) was used in place of 4-(piperidin-4-yl)benzonitrile hydrochloride (compound 1.2). m/z (ES+) 460 (M+H)+.

Sources & evidence

ORD record
ord-f781eb98f9084c219e1663ddc33644ea
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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