Hydrochloric Acid → 8-(Phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423135Notes

Reaction equation

ClC(OC(Cl)C)=O.C[N:9]1[CH2:31][C:14]2=[C:15]3[C:19](=[CH:20][CH:21]=[C:13]2[O:12][CH2:11][CH2:10]1)[N:18]([S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH:17]=[CH:16]3.CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.Cl.C(OCC)C>C(Cl)Cl>[C:25]1([S:22]([N:18]2[C:19]3[C:15](=[C:14]4[CH2:31][NH:9][CH2:10][CH2:11][O:12][C:13]4=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)(=[O:24])=[O:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 43 °C

Procedure

1-Chloroethyl chloroformate (1.0 mL, 7.0 mmol) was added to a solution of 2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 5, 0.15 g, 0.44 mmol), and 1,8-bis-(dimethylamino)-naphthalene (proton sponge) (0.056 g, 0.26 mmol) in DCM (10 mL) and the mixture was stirred at 43° C. for 1 hour. 1.0 M HCl in diethylether (2.5 mL, 2.5 mmol) was added and the mixture was evaporated. The residue was dissolved in dry MeOH (10 mL) and heated at 78° C. for 30 minutes and evaporated. The residue was dissolved in DCM and washed with water, brine, and the organic phase was dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel using MeOH:DCM:NEt3 (5:94:1) as the eluent to give the title compound (11 mg) as a light pink solid. MS m/z 329 [M+H]+.

Workup

customthe mixture was evaporated
dissolutionThe residue was dissolved in dry MeOH (10 mL)
temperatureheated at 78° C. for 30 minutes
customevaporated
dissolutionThe residue was dissolved in DCM
washwashed with water, brine
dry with materialthe organic phase was dried (MgSO4)
customevaporated
customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-f0a098dbed7c4c3bb316a036b6fda710
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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