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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 1412366
Notes
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Reaction equation

HRID 1412366 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 67010152Ethyl 2-{[6-(2-cyanophenyl)pyridin-3-yl]methyl}-3-oxohexanoateHCID 178455070HCID 178455070, compound

Product 1

HCID 670092682-(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)benzonitrileYield 21%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

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

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

Sources & evidence

ORD record
ord-94e9318936e2428cbe8e778c5e7f7ff9
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08921379B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes