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 394104노트

반응식

HRID 394104 반응식
[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]

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00d29a8c85d740e6be460d905940a601
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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