Chloroform → 7-amino-4,9-dimethyl-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one, hydrochloride
반응식
C(OC(=O)[NH:10][CH:11]1[C:25](=[O:26])[N:24]([CH3:27])[CH2:23][C:14]2[C:15]3[CH:16]=[N:17][NH:18][C:19]=3[C:20]([CH3:22])=[CH:21][C:13]=2[CH2:12]1)C1C=CC=CC=1.[H][H].C(Cl)(Cl)[Cl:32]>CO.[Pd]>[ClH:32].[NH2:10][CH:11]1[C:25](=[O:26])[N:24]([CH3:27])[CH2:23][C:14]2[C:15]3[CH:16]=[N:17][NH:18][C:19]=3[C:20]([CH3:22])=[CH:21][C:13]=2[CH2:12]1참가 물질
반응물 3
생성물 1
시약·촉매·용매 2
실험 절차
To a solution of (4,9-dimethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohepta[e]inden-7-yl)-carbamic acid benzyl ester (50 mg, 0.132 mmol) in methanol and chloroform (0.5 mL) was added 10% palladium on carbon (20 mg) under nitrogen atmosphere. The reaction mixture was brought to hydrogen atmosphere (1 atm) and stirred for 3 h. The catalyst was filtered and the solvent was evaporated to give 7-amino-4,9-dimethyl-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one, hydrochloride in almost quantitative yield. To the amine salt in dichloromethane was added disuccinimidyl carbonate (37 mg, 0.145 mmol) and triethylamine (0.11 mL, 0.8 mmol) at room temperature. After 120 min, 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one, hydrochloride (39 mg, 0.145 mmol) was added and stirring continued for 12 h. The solvent was evaporated and the crude product was purified by Prep HPLC to give 4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carboxylic acid (4,9-dimethyl-8-oxo-3,6,7,8,9,10-hexahydro-2,3,9-triaza-cyclohepta[e]inden-7-yl)-amide in 59% overall yield. MS (ESI) 502 (M+H); Rf=1.31.
후처리
- filtrationThe catalyst was filtered
- customthe solvent was evaporated
출처 및 근거
- ORD 기록
- ord-d13521365bfd45499fece9fbce40d4b1
- 출처 데이터셋
- uspto-grants-2008_06
- 특허 번호
- US07384930B2
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