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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 720151Generated: October 30, 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/720151

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 numberUS07132533B2
Source datasetuspto-grants-2006_11
ORD IDord-8ee35298b8e64cf88c2fb0c629f3ac2d
Source noteuspto-grants-2006_11