Hydrochloric Acid → HCID 44611651, compound

HRID 1645153Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21](F)[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[H-].[Na+].[CH2:33]([OH:35])[CH3:34].Cl>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][CH:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=[C:21]([O:35][CH2:33][CH3:34])[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

[4-(3-Fluoro-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (prepared by the method analogous to example 1-1, 200 mg, 0.44 mmol), sodium hydride (60% dispersed in mineral oil, 89 mg, 2.22 mmol) and ethanol (202 mg, 4.4 mmol) were dissolved in N,N-dimethylformamide (2 mL). The mixture was heated in a microwave oven at 150° C. for 40 minutes. The resulting mixture was acidified with 0.1N hydrochloric acid to pH 5 and extracted with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column (gradient elution, 0-5% methanol in dichloromethane) to afford [4-(3-ethoxy-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (180 mg, 78%). MS cald. for C20H24F3N3O5S 475, obsd. (ESI+) [(M+H)+] 476.

Workup

extractionextracted with ethyl acetate
washThe organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash column (gradient elution, 0-5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-8018a20bafb24f8a8d7bbbae6a186384
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124641B2

Reaction notes

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