Pyridine → HCID 131734352, compound

HRID 1505527Notes

Reaction equation

[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([NH2:15])[C:9]=1[F:16])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH:23]=[C:22]([S:24](Cl)(=[O:26])=[O:25])[N:21]=[CH:20]1.N1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([NH:15][S:24]([C:22]2[N:21]=[CH:20][N:19]([CH3:18])[CH:23]=2)(=[O:26])=[O:25])[C:9]=1[F:16])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

The tert-butyl-3-amino-2,6-difluorophenylcarbamate (50 mg, 0.20 mmol) prepared at Step 3 was added and dissolved into dichloromethane solvent. 1-methyl-1H-imidazole-4-sulfonyl chloride (44 uL, 0.25 mmol) and pyridine (50 uL, 0.61 mmol) were added into the reaction solution and stirred at 50° C. for 2 hours. After the reaction, the reactant was washed with 1N aqueous hydrochloric acid solution and salt water. After extraction with dichloromethane, the organic layer was dried with sulfuric anhydride magnesium and vacuum concentrated, and then refined by means of column chromatography, so that 74 mg of the target compound, tert-butyl-2,6-difluoro-3-(1-methyl-1H-imidazole-4-sulfonamido)phenylcarbamate (percentage yield: 95%), was obtained.

Workup

additionwas added
customAfter the reaction
washthe reactant was washed with 1N aqueous hydrochloric acid solution and salt water
extractionAfter extraction with dichloromethane
dry with materialthe organic layer was dried with sulfuric anhydride magnesium and vacuum
concentrationconcentrated

Sources & evidence

ORD record: ord-90d0b7f296864b728ecb56e6cdd718a6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216981B2

Reaction notes

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