Hydrochloric Acid → HCID 178521665, compound

HRID 42296Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[NH:12][CH:13]=[C:14]([C:16]3[CH:17]=[N:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:20][CH:21]=3)[N:15]=2)[CH2:6]1)=[O:4].B.O1CCCC1.Cl.C(O)C>O1CCCC1>[F:29][C:2]([F:1])([F:28])[CH:3]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]2[NH:12][CH:13]=[C:14]([C:16]3[CH:17]=[N:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[N:20][CH:21]=3)[N:15]=2)[CH2:6]1)[OH:4]

Participants

Conditions

Temperature: 65 °C

Procedure

To a room temperature solution of (±)-2,2,2-trifluoro-1-(3-(4-(2-phenylpyrimidin-5-yl)-1H-imidazol-2-yl)piperidin-1-yl)ethanone (18 mg, 0.04 mmol) in tetrahydrofuran (1 mL) was added borane-tetrahydrofuran (1M, 0.13 mL, 0.13 mmol). The reaction mixture was heated at 65° C. for four hours, cooled, treated carefully with 6 mL of 6N HCl and 2 mL of ethanol and heated at 65° C. for one hour. The cooled reaction mixture was extracted four times with ethyl acetate and the organic phase was dried over magnesium sulfate, filtered, and rotovapped. The residue was chromatographed on silica (4 g) and eluted with 1:20:80 to 5:30:70 triethylamine-isopropanol-hexanes to give the title compound as a bright yellow solid white solid; Rf 0.15 with 1:20:80 v/v triethylamine-isopropanol-hexanes; MS (ESI+) m/z 404 (M+1); H-PGDS FPBA IC50: 10 μM.

Workup

temperaturecooled
temperatureheated at 65° C. for one hour
customThe cooled reaction mixture
extractionwas extracted four times with ethyl acetate
dry with materialthe organic phase was dried over magnesium sulfate
filtrationfiltered
customThe residue was chromatographed on silica (4 g)
washeluted with 1:20:80 to 5:30:70 triethylamine-isopropanol-hexanes

Sources & evidence

ORD record: ord-015ae040653c4c8cbe0851bc2880f501
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536185B2

Reaction notes

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