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

HRID 519537

Reaction equation

HRID 519537 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17](OCC)=[O:18])=[CH:11][CH:10]=1)#[N:2].[CH2:27]([O:30][CH:31]1[CH2:36][CH2:35][CH:34]([NH:37][C:38]2[NH:42][CH:41]=[N:40][N:39]=2)[CH2:33][CH2:32]1)[CH:28]=[CH2:29]>>[O:18]=[C:17]1[C:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[C:3]([C:1]#[N:2])=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:10][CH:11]=2)=[C:22]([CH2:23][CH2:24][CH3:25])[N:39]2[N:40]=[CH:41][N:42]=[C:38]2[N:37]1[CH:34]1[CH2:33][CH2:32][CH:31]([O:30][CH2:27][CH:28]=[CH2:29])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178458503HCID 178458503, compound

Product 1

HCID 670099694'-({5-Oxo-4-[4-(prop-2-en-1-yloxy)cyclohexyl]-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl}methyl)biphenyl-2-carbonitrileYield 24%

Conditions

Temperature
250 °C

Procedure

A mixture of ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (4 g) and N-[4-(prop-2-en-1-yloxy)cyclohexyl]-4H-1,2,4-triazol-3-amine (1.3 g) was stirred at 250° C. for 20 min under microwave irradiation. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (0.7 g, 24%).

Workup

  1. customThe obtained reaction mixture
  2. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-27edf65bc6284fe99ddc88d1df49c9c7
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Linked notes

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