Methylamine → HCID 25177310, compound

Participants

Reaction Steps

(S)-4-Amino-18,20-dimethyl-10,16-dioxo-7-thia-3,5,11,15-tetraazatricyclo[15.3.1.12,6]docosa-1(20),2(22),3,5,17(21),18-hexaene-14-carboxylic acid (25 mg, 0.058 mmol) obtained in Example 2-13 and 1-hydroxybenzotriazole (24 mg, 0.175 mmol) were dissolved in N,N-dimethylformamide (580 μl). Methylamine (2.0 M tetrahydrofuran solution, 88 μl, 0.175 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (34 mg, 0.175 mmol), and diisopropylethylamine (0.073 ml, 0.42 mmol) were added to the solution. The resulting mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, and sequentially washed with a saturated aqueous sodium bicarbonate solution, water (three times), and a saturated aqueous sodium chloride solution. The washed organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by preparative thin layer silica gel chromatography (developing solvent: dichloromethane:methanol=10:1) to yield (S)-4-amino-18,20-dimethyl-10,16-dioxo-7-thia-3,5,11,15-tetraazatricyclo[15.3.1.12,6]docosa-1(20),2(22),3,5,17(21),18-hexaene-14-carboxylic acid methylamide (Compound 65) (7 mg) was obtained as a white solid material.

Provenance & Evidence