Acetonitrile → 3-Methyl-4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

HRID 517276ノート

反応式

HRID 517276 の反応式
[H-].[Na+].[O:3]=[C:4]1[NH:13][CH:12]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=2[CH3:22])[C:11]2[C:10](=[O:23])[CH2:9][CH2:8][CH2:7][C:6]=2[N:5]1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1.[C:34](#N)C>CN(C)C=O>[CH3:22][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:14]=1[CH:12]1[C:11]2[C:10](=[O:23])[CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=2)[C:4](=[O:3])[N:13]1[CH3:34])[C:18]#[N:19]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 867323954-(2,5-Dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-methylbenzonitrile

生成物 1

HCID 867324013-Methyl-4-(3-methyl-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in mineral oil, 6 mg, 0.16 mmol) is added to a solution of 4-(2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)-3-methylbenzonitrile (example 55, 60 mg, 0.13 mmol) in acetonitrile (3 mL), and the mixture is stirred at room temperature for 20 min. Methyl idodide (16 μL, 0.26 mmol) is added, and the mixture is stirred over night, diluted with N,N-dimethylformamide (1 mL) and purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 13 mg; ESI mass spectrum [M+H]+=440; Retention time HPLC: 0.65 min (X012_S01).

後処理

  1. additionMethyl idodide (16 μL, 0.26 mmol) is added
  2. stirringthe mixture is stirred over night
  3. custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom0.65 min (X012_S01)

出典と根拠

ORDレコード
ord-ac43a95975c04dc28fd0f1d1b962ba38
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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