Diisopropylethylamine → HCID 71280151, compound

Participants

Reaction Steps

A mixture of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (70 mg, 0.225 mmol), 2,2,3,3,6,9,9,10,10-nonamethyl-4,8-dioxa-3,9-disilaundecan-6-amine (112 mg, 0.338 mmol), HATU (171 mg, 0.45 mmol) and DIPEA (58 mg, 0.45 mmol) in DMF (5 mL) was stirred at room temperature for 16 hours. The mixture was poured into water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the residue was purified by column chromatography on silica gel eluting with petroleum ether/EtOAc (1:1, v/v) to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2,2,3,3,6,9,9,10,10-nonamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (65 mg, 46%) as a white solid. 1H NMR (300 MHz, DMSO): δ 9.00 (s, 1H), 8.44-8.40 (m, 1H), 8.38 (s, 1H), 7.91 (s, 1H), 7.87 (dd, J=10.2, 2.7 Hz, 1H), 7.06-7.05 (m, 1H), 4.13 (s, 3H), 3.92-3.84 (m, 1H), 1.43 (s, 3H), 0.64 (s, 18H), 0.01 (s, 12H).

Provenance & Evidence