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

HRID 517270노트

반응식

HRID 517270 반응식
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

참가 물질

5

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 867323404-(Amino(6-oxo-2-(3-(trifluoromethyl)phenylamino)cyclohex-1-enyl)methyl)-3-methylbenzonitrile hydrochloride2회

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-59338dee26114a74b39f340011b6dd70
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115093B2

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