4-(4-Methylbenzoyl)piperidine hydrochloride → [4-(Imidazo[4,5-b]pyridin-3-yl)phenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanone

HRID 2411846Notes

Reaction equation

HRID 2411846 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=O)=[CH:12][CH:11]=2)[CH:2]=1.Cl.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[O:30])=[CH:25][CH:24]=1>>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:34]3[CH2:35][CH2:36][CH:31]([C:29](=[O:30])[C:26]4[CH:25]=[CH:24][C:23]([CH3:22])=[CH:28][CH:27]=4)[CH2:32][CH2:33]3)=[O:16])=[CH:19][CH:20]=2)[CH:2]=1

Participants

3

Reactant 2

HCID 27408174-(4-Methylbenzoyl)piperidine hydrochlorideHCID 71252216Ethyl 4-(imidazo[4,5-b]pyridin-3-yl)benzoate

Product 1

HCID 71252104[4-(Imidazo[4,5-b]pyridin-3-yl)phenyl][4-(4-methylbenzoyl)piperidin-1-yl]methanoneYield 63.9%

Procedure

Using ethyl 4-(imidazo[4,5-b]pyridin-3-yl)benzoate (300 mg) described in Preparation Example 77 and (4-methylphenyl)(piperidin-4-yl)methanone hydrochloride (269 mg) and by the reaction and treatment in the same manner as in Example 170, the title compound (304.2 mg) was obtained.

Sources & evidence

ORD record
ord-7921b234519c41a182fc127401732a8c
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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