Ethylamine → HCID 136247204, compound

Participants

Reaction Steps

A solution of 4-(4-(7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)piperazin-1-yl)benzoic acid (50.4 mg, 143 μmol) in methylene chloride (1.22 mL) was treated with N,N-diisopropylethylamine (74.1 mg, 100 μL, 570 μmol), a 2M solution of ethylamine in tetrahydrofuran (86 μL, 172 μmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (49.8 mg, 260 μA mol) and 1-hydroxybenzotriazole (28.9 mg, 214 μmol). The resulting white suspension was stirred at room temperature overnight. At this time, the reaction was diluted with methylene chloride (25 mL) and methanol (5 mL), and was washed with a 1N aqueous hydrochloric acid solution (25 mL), a saturated aqueous sodium bicarbonate solution (25 mL), water (25 mL), and a saturated aqueous sodium chloride solution (25 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo onto Celite®. The product remained in the aqueous layer, so it was extracted with a solution of 10% methanol/methylene chloride (6×25 mL). The combined organics were concentrated in vacuo onto Celite®. Flash chromatography (10 g silica gel column, 1-10% methanol/methylene chloride) afforded N-ethyl-4-[4-(7-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-piperazin-1-yl]-benzamide (5.1 mg, 9.4%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.35 Hz, 3H) 3.32 (s, 4H) 3.57 (s, 3H) 3.70 (br. s., 4H) 6.25 (d, J=3.20 Hz, 1H) 6.78 (d, J=3.39 Hz, 1H) 7.00 (d, J=8.67 Hz, 2H) 7.74 (d, J=9.23 Hz, 2H) 8.19 (s, 1H) 10.88 (s, 1H). LC-MS calcd. for C20H25N6O2 [(M+H)+] 381, obsd. 381.1

Provenance & Evidence