Water → Tert-butyl 1-allyl-4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-2-carboxylate

HRID 394104ノート

反応式

HRID 394104 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][N:22]([C:25](OCC=C)=O)[CH:21]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:46])[N:13]2[C:38]1[C:43]([Cl:44])=[CH:42][CH:41]=[CH:40][C:39]=1[Cl:45].O.[CH2:48]([SnH](CCCC)CCCC)[CH2:49]CC>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][NH:22][CH:21]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:20]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:46])[N:13]2[C:38]1[C:43]([Cl:44])=[CH:42][CH:41]=[CH:40][C:39]=1[Cl:45].[CH2:25]([N:22]1[CH2:23][CH2:24][N:19]([CH2:18][C:16]2[CH:15]=[C:14]3[C:9]([CH2:10][NH:11][C:12](=[O:46])[N:13]3[C:38]3[C:43]([Cl:44])=[CH:42][CH:41]=[CH:40][C:39]=3[Cl:45])=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:17]=2)[CH2:20][CH:21]1[C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH:48]=[CH2:49]

参加物

7

反応物 3

HCID 962WaterHCID 5948TributylstannaneHCID 698511001-Allyl 2-tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-1,2-dicarboxylate

生成物 2

HCID 10282953Tert-butyl 1-allyl-4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-2-carboxylateHCID 22648143Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-2-carboxylate

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 1-allyl 2-tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-1,2-dicarboxylate (EXAMPLE AAA10, STEP A, 200 mg, 0.29 mmol) and dichlorobis(triphenylphosphine)palladium(II) (10.2 mg, 0.0146 mL) in methylene chloride (3 mL) was added water (30 μL). To this mixture was added tributyltin hydride (94 μL, 0.348 mmol) rapidly. The mixture was stirred at rt for 5 h, diluted with methylene chloride, washed with water and brine, and dried over anhydrous sodium sulfate. Removal of the solvent and subsequent purification by preparative thin layer chromatography using 5% of 2N ammonium in methanol/methylene chloride as eluent provided tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-2-carboxylate and tert-butyl 1-allyl-4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]methyl}piperazine-2-carboxylate.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customRemoval of the solvent and subsequent purification by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-00d29a8c85d740e6be460d905940a601
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

読み込み中…