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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2375117Generated: November 2, 2026

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

https://huagongshe.com/reaction/2375117

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantChloroformHCID 6212—
ReactantChlorosuccinimideHCID 31398—
Reactant8-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl esterHCID 136181612—
SolventDimethylformamideHCID 6228—
Product(2,9-Dichloro-6-oxo-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl)-carbamic acid tert-butyl esterHCID 136181636—

Reaction Conditions

Temperature60 °C

Reaction Steps

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%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07462713B2
Source datasetuspto-grants-2008_12
ORD IDord-db2fa96b11534e0dacf834a69166da8e
Source noteuspto-grants-2008_12