Triethylamine → 3-[(E)-2-(4-fluorophenyl)ethenyl]-4-methoxy-N-(2-oxopropyl)-1H-indazole-5-carboxamide

HRID 34116Notes

Reaction equation

[OH:1][CH:2]([CH3:27])[CH2:3][NH:4][C:5]([C:7]1[C:8]([O:25][CH3:26])=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[O:6].C(N(CC)CC)C>ClCCl.CS(C)=O.O>[O:1]=[C:2]([CH3:27])[CH2:3][NH:4][C:5]([C:7]1[C:8]([O:25][CH3:26])=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=1)=[O:6]

Participants

Conditions

Temperature: 40 °C

Procedure

100 mg of 3-[(E)-2-(4-fluorophenyl)-vinyl]-4-methoxy-1H-indazole-5-carboxylic acid (2-hydroxylpropyl) amide obtained by Example 825 and 300 μl of triethylamine were dissolved in a mixed solvent of 4 mL dichloromethane/1 mL dimethyl sulfoxide, added with 1 mL of a solution of 260 mg of pyridine sulfur trioxide complex in dimethyl sulfoxide under ice cooling, and the reaction solution was heated at 40° C. for 3 hours. The reaction solution was diluted with water, extracted with ethyl acetate, washed with water, and then dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:3), and then crystallized from ethyl acetate and diisopropyl ether, to afford 80 mg of the title compound as a colorless powder.

Workup

extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:3)
customcrystallized from ethyl acetate and diisopropyl ether

Sources & evidence

ORD record: ord-c21a91ae1afa4b6a9e46ab04588e2554
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429609B2

Reaction notes

Loading…