Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate → 4'-{[4-(1-Benzylpiperidin-4-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile

HRID 519748Notes

Reaction equation

HRID 519748 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[NH:19][N:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH:35]([C:41](=O)[CH2:42][CH2:43][CH3:44])[C:36](OCC)=[O:37])=[CH:30][CH:29]=1)#[N:21]>ClC1C=CC(Cl)=CC=1Cl>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:36](=[O:37])[C:35]([CH2:34][C:31]3[CH:32]=[CH:33][C:28]([C:23]4[C:22]([C:20]#[N:21])=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:29][CH:30]=3)=[C:41]([CH2:42][CH2:43][CH3:44])[N:19]3[N:18]=[CH:17][N:16]=[C:15]23)[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 670086211-benzyl-N-(1H-1,2,4-triazol-5-yl)-piperidine-4-amine

Product 1

HCID 670101534'-{[4-(1-Benzylpiperidin-4-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileYield 30.4%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A solution of 1-benzyl-N-(1H-1,2,4-triazol-5-yl)-piperidine-4-amine (7.53 g) and ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (14.41 g) in 1,2,4-trichlorobenzene (20 mL) was stirred at 195° C. for 2 days. The reaction mixture was cooled to room temperature and purified by silica gel chromatography [eluent: hexane/ethyl acetate=65/35→50/50 (volume ratio)] to give the title compound (4.82 g, 30%) as a brown amorphous compound.

Workup

  1. custompurified by silica gel chromatography [eluent: hexane/ethyl acetate=65/35→50/50 (volume ratio)]

Sources & evidence

ORD record
ord-a9c4feb63b1248d89e08bba26f038829
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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