Ethanolamine → HCID 86713715, compound

HRID 1406043Notes

Reaction equation

CS(O[C@@H:6]1[CH2:9][CH2:8][C@@H:7]1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])(=O)=O.[NH2:21][CH2:22][CH2:23][OH:24]>C(OCC)(=O)C>[F:18][C:17]([F:20])([F:19])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][C@@H:7]1[CH2:8][CH2:9][C@H:6]1[NH:21][CH2:22][CH2:23][OH:24]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of C8 (500 mg, 1.61 mmol) and 2-aminoethanol (5 mL) was heated at 90° C. for 18 hours, then at 100° C. for an additional 24 hours. The reaction was cooled, diluted with ethyl acetate (100 mL) and washed with aqueous sodium hydroxide solution (1 M, 5×50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via HPLC (Column: Phenomenex Luna C18(2), 5 μm; Mobile phase A: 0.1% formic acid in water; Mobile phase B: 0.1% formic acid in methanol; Gradient: 5% to 100% B) afforded the title compound as a solid. Yield; 191 mg, 0.694 mmol, 43%. LCMS m/z 276.3 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.49 (br s, 1H), 7.56 (br d, J=7.6 Hz, 1H), 7.44-7.50 (m, 1H), 7.04 (br dd, J=7.6, 7.6 Hz, 1H), 6.92 (br d, J=8.4 Hz, 1H), 4.90-4.97 (m, 1H), 3.75-3.90 (m, 3H), 2.99-3.15 (m, 2H), 2.46-2.56 (m, 1H), 2.21-2.31 (m, 1H), 1.90-2.02 (m, 1H), 1.77-1.89 (m, 1H).

Workup

temperatureThe reaction was cooled
washwashed with aqueous sodium hydroxide solution (1 M, 5×50 mL)
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via HPLC (Column: Phenomenex Luna C18(2), 5 μm; Mobile phase A: 0.1% formic acid in water; Mobile phase B: 0.1% formic acid in methanol; Gradient: 5% to 100% B)

Sources & evidence

ORD record: ord-e5e32b0ddbb24a9cb8fba11ee6fea4e0
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916564B2

Reaction notes

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