Potassium Carbonate → 4-(1-(3-(Trifluoromethyl)phenyl)-2,5-dioxo-3-((tetrahydrofuran-3-yl)methyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

HRID 517244Notes

Reaction equation

HRID 517244 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[NH:17][CH:16]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[C:15]2[C:14](=[O:26])[CH2:13][CH2:12][CH2:11][C:10]=2[N:9]1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=1.Br[CH2:38][CH:39]1[CH2:43][CH2:42][O:41][CH2:40]1>CN(C)C=O>[F:35][C:33]([F:36])([F:34])[C:29]1[CH:28]=[C:27]([N:9]2[C:10]3[CH2:11][CH2:12][CH2:13][C:14](=[O:26])[C:15]=3[CH:16]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)[N:17]([CH2:38][CH:39]3[CH2:43][CH2:42][O:41][CH2:40]3)[C:8]2=[O:7])[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 141734223-(Bromomethyl)oxolaneHCID 86732326HCID 86732326, compound

Product 1

HCID 867323654-(1-(3-(Trifluoromethyl)phenyl)-2,5-dioxo-3-((tetrahydrofuran-3-yl)methyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (67 mg, 0.486 mmol) is added to a solution of 4-(2,5-dioxo-1-(3-(tri-fluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-benzonitrile (example 1, 100 mg, 0.243 mmol) in N,N-dimethylformamide (3 mL). 3-(Bromomethyl)tetrahydrofuran (60 mg, 0.365 mmol) is added, and the mixture is stirred at room temperature for 1 h and purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 12 mg; ESI mass spectrum [M+H]+=496; Retention time HPLC: 0.91 min (Z011_S03).

Workup

  1. custompurified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom0.91 min (Z011_S03)

Sources & evidence

ORD record
ord-0373ef94d1eb4504b9e7d77f3580ccf0
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…