Ammonium formate → HCID 20764011, compound

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Reaction Steps

In a nitrogen-purged, round-bottomed flask, (R)-2-[4-(4-{2-[2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethylamino]-ethoxy}-phenyl)-oxazol-2-yl]-1-pyrrolidin-1-yl-ethanone 1-1A (200 mg, 0.42 mmol) was dissolved in methanol (15 ml). 10% Pd/C (160 mg, 80 wt %), and ammonium formate (321 mg, 5.1 mmol) were then added sequentially. The reaction mixture was stirred overnight, and was then filtered through a pad of diatomaceous earth, and the filter cake rinsed with ethyl acetate. The filtrate was concentrated to a white solid, which was taken up in ethyl acetate and saturated aqueous sodium carbonate, and extracted. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford a crude solid. This material was suspended in diethylether and isolated by vacuum filtration to afford a crystalline solid 1-1B (110 mg, 59% yield). This material was then converted to the corresponding hydrochloride salt. Analytical data for the HCl salt: LRMS ([M+H]+): 437.4. 1H NMR: (400 MHz, CD3OD): δ1.91 (m, 2H), 2.02 (m, 2H), 3.37-3.29 (m, 2H), 3.45 (m, 2H), 3.54-3.63 (m, 5H), 3.97 (s, 2H), 4.37 (t, 2H, J=4.8 Hz), 5.38 (dd, 1H, J=3.2,10.4 Hz), 7.07 (dd, 2H, J=2.8, 9.6 Hz), 7.69 (dd, 2H, J=1.8, 6.4 Hz), 8.14 (m, 2H), 8.75 (m, 1H), 8.86 (d, 1H, J=6.0 Hz), 8.99 (m, 1H). Preparation for 2-[4-(4-{2-[2(R)-Hydroxy-2-(6-methyl-pyridin-3-yl)-ethylamino]-ethoxy}-phenyl)-oxazol-2-yl]-N,N-dimethyl-acetamide (1-1C)

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