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

HRID 517218ノート

反応式

HRID 517218 の反応式
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

参加物

5

反応物 3

HCID 962WaterHCID 23676156Sodium t-butoxideHCID 867323361-((4-Bromo-2-methoxyphenyl)(2-ethoxy-6-oxocyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)-urea2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d792bca3a3514164a6ef4cfc0e4a7fac
出典データセット
uspto-grants-2015_08
特許番号
US09115093B2

反応ノート

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