Potassium Carbonate → 2-(3,5-Dichlorophenyl)-1,3-dioxo-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic Acid Tert-Butyl Ester

HRID 49976

反応式

HRID 49976 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O:14][C:15]([CH:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1)=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:26]([O:25][C:23]([N:19]1[CH2:20][CH2:21][N:22]2[C:10](=[O:11])[N:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)[C:15](=[O:14])[CH:17]2[CH2:18]1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 944603,5-Dichlorophenyl isocyanateHCID 114026711-tert-Butyl 3-ethyl piperazine-1,3-dicarboxylate

生成物 1

HCID 224792022-(3,5-Dichlorophenyl)-1,3-dioxo-hexahydro-imidazo[1,5-a]pyrazine-7-carboxylic Acid Tert-Butyl Ester収率 136.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

3,5-Dichlorophenyl isocyanate (2.85 g, 15.2 mmol) was added portionwise to a mixture of piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (2.61 g, 10.1 mmol, prepared as described in Bioorg. Med. Chem. Lett. 1999, 9, 1121-6) and potassium carbonate (1.68 g, 12.1 mmol) in DCM (30 mL) at 5° C. After 30 min at 5° C., the reaction mixture was stirred at 20° C. for 48 h. The white precipitate was discarded and the filtrate concentrated in vacuo to give an oil (5.5 g) which was chromatographed over silica gel (CH2Cl2), to yield the above compound (2.77 g) as a white solid. Mp=144° C.

後処理

  1. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-e46489ca004e4266b9dcc6048fdf3da3
出典データセット
uspto-grants-2004_03
特許番号
US06710064B2

関連ノート

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