Pyridine → HCID 11991895, compound

HRID 2386185Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[O:16][C:17]([C:20]([NH2:22])=O)=[CH:18][N:19]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[O:16][C:17]([C:20]#[N:22])=[CH:18][N:19]=2)=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 23 °C

Procedure

2-(7-Phenylheptanoyl)oxazole-5-carboxamide (35 mg, 0.117 mmol) was dissolved in 1,4-dioxane (3 mL) and pyridine (2.5 equiv) and trifluoroacetic anhydride (1.3 equiv) were added. The reaction mixture stirred for 2 h at 23° C. The mixture was diluted with CH2Cl2 and the combined organic layers were washed with saturated aqueous NaCl and dried over Na2SO4. Evaporation in vacuo yielded the crude nitrile, which was purified by flash chromatography (2-20% EtOAc/hexanes) to afford the title compound as a clear oil: 1H NMR (CDCl3, 600 MHz) δ 7.84 (s, 1H), 7.28-7.25 (m, 2H), 7.18-7.16 (m, 3H), 3.07 (t, 2H, J=7.8 Hz), 2.60 (t, 2H, J=7.8 Hz), 1.77-1.72 (m, 2H), 1.65-1.60 (m, 2H), 1.41-1.37 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 188.1, 159.5, 143.4, 139.0, 129.3, 129.1, 127.3, 126.5, 109.1, 40.5, 36.7, 32.1, 29.8, 29.7, 24.3; MALDI-FTMS m/z 281.1293 (M+H−, C17H17N2O2, requires 281.1295).

Workup

washthe combined organic layers were washed with saturated aqueous NaCl
dry with materialdried over Na2SO4
customEvaporation in vacuo
customyielded the crude nitrile, which
customwas purified by flash chromatography (2-20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-2e213faad4df493bae8aa5dd1f8f7f04
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268817B2

Reaction notes

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