Sodium t-butoxide → 4-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile

HRID 517230Notes

Reaction equation

HRID 517230 reaction equation
CC(C)([O-])C.[Na+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:30]2[C:35](=[O:36])[CH2:34][CH2:33][CH2:32][C:31]=2OCC)[NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:11][CH:10]=1)#[N:8]>C(#N)C>[O:18]=[C:17]1[NH:16][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=2)[C:30]2[C:35](=[O:36])[CH2:34][CH2:33][CH2:32][C:31]=2[N:19]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=1

Participants

4

Reactant 2

HCID 23676156Sodium t-butoxideHCID 903737891-((4-Cyanophenyl)-(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Product 1

HCID 867323264-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium tert-butoxide (2.55 g, 26.5 mmol) is added to a mixture of 1-((4-cyanophenyl)-(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 5, 10.1 g, 22.1 mmol) and acetonitrile (100 mL). After 20 min the mixture is filtered and the precipitate is washed with acetonitrile and methyl tert-butyl ether. The precipitate is mixed with water (300 mL) and the suspension is stirred for 1 h. The precipitate is filtered again and dried under reduced pressure. Yield: 5.24 g; ESI mass spectrum [M+H]+=412; Retention time HPLC: 0.88 min (Z018_S04).

Workup

  1. filtrationAfter 20 min the mixture is filtered
  2. washthe precipitate is washed with acetonitrile and methyl tert-butyl ether
  3. additionThe precipitate is mixed with water (300 mL)
  4. filtrationThe precipitate is filtered again
  5. customdried under reduced pressure
  6. custom0.88 min (Z018_S04)

Sources & evidence

ORD record
ord-3f66a8cd214e497eb6605a41e4404ac2
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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