Diisopropylethylamine → HCID 178521900, compound

Participants

Reaction Steps

To a stirred solution of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (250 mg, 0.67 mmol; example 5.1) in dry DMF (12 mL) was added dry DIPEA (0.375 ml, 2.32 mmol) followed by HATU (510 mg, 1.34 mmol) at 0° C. Then the reaction mixture was allowed to warm to rt and stirred for 45 min at that temperature. TLC shows total consumption of acid and formation of a new spot. 4-(1H-Tetrazol-5-yl)-phenylamine (162.5 mg, 1.02 mmol) was added to this reaction mixture at 0° C. Then the cooling bath was removed and the reaction mixture was stirred at room temperature for 16 h. TLC shows total consumption of [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid and DMF was removed in vacuo at 50° C. It was then diluted with H2O (15 ml). Aqueous layer was extracted with EtOAc (4×20 mL) and combined organic layers were washed with brine (20 ml), dried over Na2SO4 and concentrated in vacuo. Crude product (355.0 mg) was subjected to column chromatography [SiO2 (230-400 mesh), McOH:DCM 5:95] to give the title compound as brownish sticky solid. Yield (170 mg, 52%). MS: m/e=516.0 [M+H+].

Provenance & Evidence