Sodium Hydroxide → 1-(1H-indazol-4-yl)-3-[(cis)-3-(4-methyl-1,3-thiazol-2-yl)cyclopentyl]urea

Participants

Reaction Steps

A solution of Example 120C (89 mg, 0.41 mmol), N,N-dimethylformamide (3 mL), diisopropylethylamine (0.15 mL, 0.85 mmol) and methyl 4-((2,5-dioxopyrrolidin-1-yloxy)carbonylamino)-1H-indazole-1-carboxylate (prepared as in Org. Proc. Res. Dev., 2007, 11, 578; 135 mg, 0.41 mmol) was stirred at room temperature for 10 minutes. Methanol (6 mL) and 5N aqueous NaOH (0.24 mL, 1.2 mmol) were added and stirring continued for 2 hours at room temperature. The reaction mixture was diluted with water (10 mL), concentrated to half the volume, and extracted with ethyl acetate (2×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% of methanol/ethyl acetate (1:10) in hexanes) to obtain the title compound (60 mg, 43%) and Example 119 (28 mg, 20%). MS (ESI+) M/Z 342 [M+H]+.

Provenance & Evidence