N,N-Diethylaniline → 2-(5-{[4-(4-{[Tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}pyridin-2-yl)benzonitrile

HRID 2048395Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16]([C:22](=O)[CH2:23][CH2:24][CH3:25])[C:17]([O:19]CC)=O)=[CH:11][CH:10]=1)#[N:2].[Si:27]([O:34][CH:35]1[CH2:40][CH2:39][CH:38]([NH:41][C:42]2[NH:46][CH:45]=[N:44][N:43]=2)[CH2:37][CH2:36]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(N(CC)C1C=CC=CC=1)C>C(OCC)(=O)C>[Si:27]([O:34][CH:35]1[CH2:40][CH2:39][CH:38]([N:41]2[C:17](=[O:19])[C:16]([CH2:15][C:12]3[CH:11]=[CH:10][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]#[N:2])=[N:14][CH:13]=3)=[C:22]([CH2:23][CH2:24][CH3:25])[N:43]3[N:44]=[CH:45][N:46]=[C:42]23)[CH2:37][CH2:36]1)([C:30]([CH3:33])([CH3:31])[CH3:32])([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of ethyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxohexanoate (1.8 g), N-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-4H-1,2,4-triazol-3-amine (1.4 g) and N,N-diethylaniline (30 mL) was stirred at 180° C. for 8 hr. The obtained reaction mixture was diluted with ethyl acetate, washed 3 times with 1 N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.42 g, 21%).

Workup

customThe obtained reaction mixture
washwashed 3 times with 1 N hydrochloric acid and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-df4363ec5a3a40b49a83d62cbe7678ba
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592431B2

Reaction notes

Loading…