Triethylamine → 4-(1-(3-(Trifluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile

HRID 59650Notes

Reaction equation

HRID 59650 reaction equation
Cl.[NH2:2][CH:3]([C:16]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:17]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[S:12]([CH3:15])(=[O:14])=[O:13].[C:34](N1C=CN=C1)(N1C=CN=C1)=[O:35].C(N(CC)CC)C>C(#N)C>[O:35]=[C:34]1[NH:2][CH:3]([C:4]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=2[S:12]([CH3:15])(=[O:14])=[O:13])[C:16]2[C:21](=[O:22])[CH2:20][CH2:19][CH2:18][C:17]=2[N:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 118692887HCID 118692887, compound2×

Product 1

HCID 867323284-(1-(3-(Trifluoromethyl)phenyl)-2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-(methylsulfonyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-{amino-[6-oxo-2-(3-trifluoromethyl-phenylamino)-cyclohex-1-enyl]-methyl}-3-methanesulfonyl-benzonitrile hydrochloride (INTERMEDIATE 17, 529 mg, 0.95 mmol) in acetonitrile (5.0 mL) is added 1,1′-carbonyldiimidazole (192 mg, 1.19 mmol) and triethylamine (33 μL, 0.24 mmol). After stirring at room temperature over night, the reaction mixture is concentrated under reduced pressure. The residue is treated with water and the precipitate is filtered off, washed with water and dried. Yield: 468 mg. ESI mass spectrum: [M+H]+=490; Retention time HPLC: 0.57 min (X012_S01).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. additionThe residue is treated with water
  3. filtrationthe precipitate is filtered off
  4. washwashed with water
  5. customdried
  6. custom0.57 min (X012_S01)

Sources & evidence

ORD record
ord-2d2423e24a2d4650854a7e68f14f7cc4
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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