1-Hydroxybenzotriazole → HCID 25177018, compound

Participants

Reaction Steps

5-{2-Amino-6-[2-(2,4-diaminobutyrylamino)ethylsulfanyl]pyrimidin-4-yl}-2,4-dimethylbenzoic acid tri(trifluoroacetate) (60 mg, 0.079 mmol) obtained in Step 3 of Example 3-8 and 1-hydroxybenzotriazole (43 mg, 0.316 mmol) were dissolved in N,N-dimethylformamide (46 ml). 1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (61 mg, 0.316 mmol) and diisopropylethylamine (8.3 μl, 0.473 mmol) were added to the solution, and stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, and then sequentially washed with a saturated aqueous sodium bicarbonate solution, water (three times), and a saturated aqueous sodium chloride solution. After the organic layer was dried over anhydrous sodium sulfate, the inorganic salt was filtered and washed with ethyl acetate. The filtrate and washing solution were combined together, and concentrated under reduced pressure. The resulting residue was purified by preparative thin layer silica gel chromatography (developing solvent: dichloromethane:methanol=10:1) to yield N-(4-amino-18,20-dimethyl-11,16-dioxo-7-thia-3,5,10,15-tetraazatricyclo[15.3.1.12,6]docosa-1(20),2(22),3,5,17(21),18-hexaen-12-yl)-2,2,2-trifluoroacetamide (Compound 75) (12 mg) as a white solid material.

Provenance & Evidence