Chloroform → 7-amino-4,9-dimethyl-6,7,9,10-tetrahydro-3H-2,3,9-triaza-cyclohepta[e]inden-8-one, hydrochloride
反応式
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]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 2
実験手順
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.
後処理
- filtrationThe catalyst was filtered
- customthe solvent was evaporated
出典と根拠
- ORDレコード
- ord-b820d985be2947608566d28c0345a98a
- 出典データセット
- uspto-grants-2008_06
- 特許番号
- US07384931B2
反応ノート
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