Methyl iodide → HCID 44611780, compound

HRID 1966869Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].CI.[C:30](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([N:15]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)(=[O:17])=[O:18])[CH3:30])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of [(R)-4-(3-chloro-4-fluoro-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (150 mg, 0.36 mmol, prepared as described in example 4-1, 1st step) in acetonitrile (10 mL) was added methyl iodide (154 mg, 1.1 mmol) and potassium carbonate (151 mg, 1.1 mmol). The reaction mixture was stirred at 65° C. for 5 hours, then cooled to room temperature and filtered through a glass funnel. The filtrate was evaporated under reduced pressure and purified by column chromatography (gradient elution, 0-10% methanol in dichloromethane) to afford {(R)-4-[(3-chloro-4-fluoro-benzenesulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (150 mg, 96%) as a yellow solid. MS cald for C18H21ClN3O4S 429, obsd. (ESI+) [(M+H)+]: 430.

Workup

temperaturecooled to room temperature
filtrationfiltered through a glass funnel
customThe filtrate was evaporated under reduced pressure
custompurified by column chromatography (gradient elution, 0-10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-be387fdb4f90401582c6f8010a756c71
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420675B2

Reaction notes

Loading…