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

HRID 49976

반응식

HRID 49976 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

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.

후처리

  1. concentrationthe filtrate concentrated in vacuo

출처 및 근거

ORD 기록
ord-e46489ca004e4266b9dcc6048fdf3da3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710064B2

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