Ethanolamine → HCID 57664732, compound

HRID 1717403Notes

Reaction equation

[CH2:1]([NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)=[C:15]([C:26](OCC)=[O:27])[N:14]=[N:13]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:31]([CH2:33][NH2:34])[OH:32]>O>[CH2:1]([NH:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:16]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=3)=[C:15]([C:26]([NH:34][CH2:33][CH2:31][OH:32])=[O:27])[N:14]=[N:13]2)=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 1-{4-[(ethylamino)carbonyl]phenyl}-5-[(3-methylphenoxy)methyl]-1H-1,2,3-triazole-4-carboxylate (720 mg) obtained in Example 515a) and ethanolamine (2.5 ml) was heated at 50° C. for 14 hr. Water was added to the reaction mixture, and the mixture was extracted with chloroform, and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=95/5) and recrystallized from ethyl acetate to give the title compound as a colorless powder (680 mg).

Workup

extractionthe mixture was extracted with chloroform
washwashed with saturated brine
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column (ethyl acetate to ethyl acetate/methanol=95/5)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-60a1d03ddf414aa387d85a15d3034e6c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803822B2

Reaction notes

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