Acetic Acid → HCID 58804027, compound

HRID 349274Notes

Reaction equation

[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([C:18]([C:20]2[C:21]([CH2:32][O:33]C3CCCCO3)=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:19])[N:9]=[CH:8]1.C(O)(=O)C.O>C1COCC1>[F:47][C:2]([F:1])([F:48])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:42]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([C:18]([C:20]2[C:21]([CH2:32][OH:33])=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=[O:19])[N:9]=[CH:8]1

Participants

Conditions

Temperature: 60 °C

Procedure

Dissolve [1-(3,5-Bis-trifluoromethyl-benzyl)-5-pyridin-3-yl-1H-imidazol-4-yl]-[5-(2-chloro-phenyl)-3-(tetrahydro-pyran-2-yloxymethyl)-isoxazol-4-yl]-methanone (0.136 g, 0.20 mmol) in THF (1.5 mL), add acetic acid (1.5 mL) and H2O (0.5 mL). Attach a reflux condenser and stir 20 hours in a 60° C. oil bath. Concentrate under vacuum, neutralize with saturated aqueous NaHCO3, and extract with EtOAc. Dry over MgSO4, filter through paper, and concentrate under vacuum. Recrystallize in ether/hexane (1:10) to give the title compound: MS (ES) 607.1 (M+1), 1H NMR (CDCl3) δ 8.69 (br s, 1H), 8.58 (br s, 1H), 7.82 (s, 1H), 7.64 (m, 2H), 7.44–7.28 (m, 5H), 7.23 (s, 2H), 5.14 (s, 2H), 4.76 (s, 2H).

Workup

concentrationConcentrate under vacuum
extractionextract with EtOAc
dry with materialDry over MgSO4
filtrationfilter through paper
concentrationconcentrate under vacuum
customRecrystallize in ether/hexane (1:10)

Sources & evidence

ORD record: ord-80ee04e80c514364ac60feb98db683c0
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179804B2

Reaction notes

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