Water → 4-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-methylbenzonitrile

HRID 517270Notes

Reaction equation

HRID 517270 reaction equation
Cl.[NH2:2][CH:3]([C:13]1[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[CH3:12].[CH2:31](N(CC)CC)C.[OH2:38]>C(#N)C>[O:38]=[C:31]1[NH:2][CH:3]([C:4]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=2[CH3:12])[C:13]2[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]=2[N:20]1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 867323404-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-methylbenzonitrile hydrochloride2×

Product 1

HCID 867323954-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-methylbenzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-methylbenzonitrile hydrochloride (intermediate 52, 1.06 g, 2.43 mmol), 1,1-carbonyl-diimidazole (495 mg, 3.05 mmol) and triethylamine (685 μL, 4.87 mmol) in acetonitrile (10 mL) is stirred at room temperature over night. Water ist added, and the mixture is extracted with dichloromethane. The phases are separated, and the organic layer is concentrated under reduced pressure. The residue is by purified by preparative HPLC (Waters it) Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 364 mg; ESI mass spectrum [M+H]+=426; Retention time HPLC: 0.65 min (X012_S01).

Workup

  1. extractionthe mixture is extracted with dichloromethane
  2. customThe phases are separated
  3. concentrationthe organic layer is concentrated under reduced pressure
  4. customby purified by preparative HPLC (Waters it) Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  5. custom0.65 min (X012_S01)

Sources & evidence

ORD record
ord-59338dee26114a74b39f340011b6dd70
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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