1-Hydroxybenzotriazole → HCID 25177083, compound

Participants

Reaction Steps

1-Hydroxybenzotriazole (888 mg, 6.57 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (2.5 g, 13.15 mmol), and diisopropylethylamine (11.5 ml, 65.74 mmol) were dissolved in tetrahydrofuran (500 ml). A tetrahydrofuran (160 ml) solution of 5-{2-amino-6-[2-(2,4-diaminobutyrylamino)ethylsulfanyl]pyrimidin-4-yl}-2,4-dimethylbenzoic acid tri(trifluoroacetate) (1.0 g, 1.31 mmol) obtained in Step 3 above was dropwise added to the above solution over 30 minutes. The resulting mixture was stirred for four hours. The reaction solution was diluted with ethyl acetate (2 l), and sequentially washed with a saturated aqueous sodium bicarbonate solution (100 ml) and a saturated aqueous sodium chloride solution (100 ml). 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 silica gel column chromatography (developing solution: dichloromethane:methanol=10:1) to yield 4,12-diamino-18,20-dimethyl-7-thia-3,5,10,15-tetraazatricyclo[15.3.1.12,6]docosa-1(20),2(22),3,5,17(21),18-hexaene-11,16-dione (Compound 73) (119 mg) as a white solid material.

Provenance & Evidence