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

HRID 1688485Notes

Reaction equation

HRID 1688485 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].[O:27]1[CH2:32][CH2:31][CH2:30][CH:29]([NH:33][C:34]2[NH:38][CH:37]=[N:36][N:35]=2)[CH2:28]1>>[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:35]2[N:36]=[CH:37][N:38]=[C:34]2[N:33]1[CH:29]1[CH2:30][CH2:31][CH2:32][O:27][CH2:28]1

Participants

3

Reactant 2

HCID 10020734Ethyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178420922HCID 178420922, compound

Product 1

HCID 670100534'-{[5-oxo-7-propyl-4-(tetrahydro-2H-pyran-3-yl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileYield 63.2%

Conditions

Temperature
250 °C

Procedure

A mixture of ethyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxohexanoate (0.37 g) and N-(tetrahydro-2H-pyran-3-yl)-4H-1,2,4-triazol-3-amine (0.088 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 (0.15 g, 63%).

Workup

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

Sources & evidence

ORD record
ord-1874f71b0e1d41fc8d8dc43f4ec372a7
Source dataset
uspto-grants-2012_04
Patent number
US08148383B2

Reaction notes

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