Water → 4-(4-Bromo-2-methoxyphenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

HRID 517218노트

반응식

HRID 517218 반응식
CC(C)([O-])C.[Na+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:29]2[C:34](=O)[CH2:33][CH2:32][CH2:31][C:30]=2[O:36]CC)[NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)=[O:17])=[C:10]([O:39][CH3:40])[CH:9]=1.O>C(#N)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[C:29]3[C:30](=[O:36])[CH2:31][CH2:32][CH2:33][C:34]=3[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=3)[C:16](=[O:17])[NH:15]2)=[C:10]([O:39][CH3:40])[CH:9]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 867323361-((4-Bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea2회

생성물 1

HCID 867323374-(4-Bromo-2-methoxyphenyl)-1-(3-(trifluoromethyl)phenyl)-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Sodium tert-butoxide (175 mg, 1.82 mmol) is added to a solution of 1-((4-bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea (intermediate 49, 760 mg, 1.40 mmol) in acetonitrile (4 mL), and the mixture is shaked in an ultrasound bath for 20 min Water is added, and the mixture is extracted with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 41 mg; ESI mass spectrum [(79Br)-M+H]+=495, [(81Br)-M+H]+=497; Retention time HPLC: 0.96 min (Z011_S03).

후처리

  1. extractionthe mixture is extracted with dichloromethane
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  5. custom0.96 min (Z011_S03)

출처 및 근거

ORD 기록
ord-d792bca3a3514164a6ef4cfc0e4a7fac
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115093B2

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