Diisopropylethylamine → HCID 59745104, compound

Participants

Reaction Steps

(E)-(3-Chloro-4-methanesulfonyl-phenyl)-cyclopentyloxyimino-acetic acid (prepared as in Example 1, 100 mg, 0.29 mmol), 1-propyl-1H-pyrazol-3-ylamine (40 μL, 0.29 mmol) and N,N-diisopropylethylamine (151 μL, 0.87 mmol) were combined in methylene chloride (1.5 mL) and cooled in an ice bath. O-(7-Azabenzotriazole-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (110 mg, 0.29 mmol) was added and the ice bath was removed. After stirring 2 h, the reaction mixture was evaporated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution (1 mL) and extracted with chloroform (2×3 mL). The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 33% ethyl acetate/hexanes) to afford (E)-2-(3-chloro-4-methanesulfonyl-phenyl)-2-cyclopentyloxyimino-N-(1-propyl-1H-pyrazol-3-yl)-acetamide (88 mg, 67%) as a white solid after lyophilization from aqueous acetonitrile: LC-MS (ESI) m/e calcd for C20H25ClN4O4S [M+] 452.13, found 453 [M+H+]; H1-NMR (400 MHz, CDCl3) δ ppm 0.98 (t, J=7.5 Hz, 3H, CH3), 1.64 (m, 4 H, 2×CH2), 1.87 (m, 6 H, 3×CH2), 3.29 (s, 3 H, SO2CH3), 4.01 (st, J=7.0 Hz, 32H, NCH2), 4.88 (m, 1 H, OCH), 6.69 (d, J=2.3 Hz, 1 H, Ar), 7.31 (d, J=2.3 Hz, 1 H, Ar), 7.55 (dd, Jo=8.2, Jm=1.6 Hz, 1 H, Ar), 7.66 (d, Jm=1.6 Hz, 1 H, Ar), 8.18 (d, Jo=8.2 Hz, 1 H, Ar), 9.16 (s, 1 H, NH).

Provenance & Evidence