Water → (2,9-Dichloro-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

HRID 2375117노트

반응식

HRID 2375117 반응식
COC(C1[NH:6][C:7]2[CH:8]=[C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:10]=[C:11]3[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]=1[C:12]=23)=O.[Cl:27]N1C(=O)CCC1=O.O.[CH:36]([Cl:39])(Cl)Cl>CN(C)C=O>[C:23]([O:22][C:20](=[O:21])[NH:19][C:9]1[CH:10]=[C:11]2[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]3=[C:36]([Cl:39])[NH:6][C:7]([C:8]=1[Cl:27])=[C:12]23)([CH3:26])([CH3:25])[CH3:24]

참가 물질

6

반응물 4

HCID 962WaterHCID 6212Chloroform3회HCID 31398ChlorosuccinimideHCID 1361816128-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester

생성물 1

HCID 136181636(2,9-Dichloro-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
60 °C

실험 절차

To a solution of Intermediate 147(c) of Example 147 (1.5 g, 5 mmol) in CHCl3 (10 mL) and N,N-dimethylformamide (15 mL), was added N-chlorosuccinimide (701 mg, 5.25 mmol). The mixture was heated to 60° C. and stirred for 3 hours. Chloroform, N,N-dimethylformamide and water were added. Following extractive work-up with chloroform, the organic layer was dried over Na2SO4 and filtered. Evaporation of the volatile components gave a deep brown residue to which methanol was added. Filtration and collection of the solids gave the title compound (648 mg) as deep brown solid whose purity by NMR and HPLC was estimated to be about 70%.

후처리

  1. dry with materialthe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. customEvaporation of the volatile components
  4. customgave a deep brown residue to which methanol
  5. additionwas added
  6. filtrationFiltration and collection of the solids

출처 및 근거

ORD 기록
ord-db2fa96b11534e0dacf834a69166da8e
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462713B2

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