Hydrochloric Acid → HCID 67244330, compound

HRID 2423356Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12](N)=[CH:11][C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21].N1C=CC=CC=1.Cl>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([S:20]([CH3:19])(=[O:22])=[O:21])=[CH:11][C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A dried 25 ml of two-neck round bottom flask was filled with argon gas. The solution of (4-amino-2,5-difluorobenzyl)-carbamic acid t-butyl ester (0.43 g, 1.66 mmol) in methylenechloride was put into the flask and then cooled to 0° C. To the solution were added methanesulfonylchloride (1.2 eq, 1.99 mmol, 0.16 ml) and pyridine (excess, 0.5 ml) slowly, the mixture solution was refluxed for 12 hours. After confirming the completion of the reaction with TLC, the reaction solution was acidified by 10% HCl, extracted with methylenechloride, washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=2/1) to yield a white solid (0.41 g, 73.5%).

Workup

additionA dried 25 ml of two-neck round bottom flask was filled with argon gas
temperaturethe mixture solution was refluxed for 12 hours
customthe completion of the reaction with TLC
extractionextracted with methylenechloride
washwashed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-96ca05fa012342d69fe95e07e692d588
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960584B2

Reaction notes

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