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

HRID 519519Notes

Reaction equation

HRID 519519 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:21](=O)[CH2:22][CH2:23][CH2:24][CH3:25])[C:17](OC)=[O:18])=[CH:11][CH:10]=1)#[N:2].[O:27]1[CH2:32][CH2:31][CH:30]([NH:33][C:34]2[NH:38][CH:37]=[N:36][N:35]=2)[CH2:29][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:21]([CH2:22][CH2:23][CH2:24][CH3:25])[N:35]2[N:36]=[CH:37][N:38]=[C:34]2[N:33]1[CH:30]1[CH2:29][CH2:28][O:27][CH2:32][CH2:31]1

Participants

3

Reactant 2

HCID 10807723Methyl 2-[(2'-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoateHCID 178420923HCID 178420923, compound

Product 1

HCID 670084574'-{[5-oxo-7-butyl-4-(tetrahydro-2H-pyran-4-yl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrileYield 62.4%

Conditions

Temperature
250 °C

Procedure

A mixture of methyl 2-[(2′-cyanobiphenyl-4-yl)methyl]-3-oxoheptanoate (1.3 g) and N-(tetrahydro-2H-pyran-4-yl)-4H-1,2,4-triazol-3-amine (0.3 g) was stirred at 250° C. for 15 min under microwave irradiation. The obtained reaction mixture was purified by silica gel column chromatography to give the title compound as a colorless solid (0.52 g, 62%).

Workup

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

Sources & evidence

ORD record
ord-29a32de4f0654455b2c6f0b8b20aa5f6
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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