反应详情

A mixture of 3-[3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxyamine (265 mg, 0.66 mmol, prepared in the preceding step) and 1H-pyrazole-1-carboxamidine hydrochloride (196 mg, 1.33 mmol) in anhydrous N,N-dimethylformamide (3 mL) was stirred at ambient temperature for 2.5 h. Additional 1H-pyrazole-1-carboxamidine hydrochloride (97 mg, 0.66 mmol) was added and the reaction was stirred at ambient temperature for 3 days. N,N-Dimethylformamide was removed in vacuo, then acetonitrile (1 mL) was added to precipitate excess 1H-pyrazole-1-carboxamidine hydrochloride. The mixture was filtered and the filtrate was concentrated in vacuo. The residual oil was partitioned between diethyl ether (20 mL) and water (20 mL). The aqueous layer was washed with diethyl ether (2×20 mL). The aqueous layer was neutralized (pH 7) with 2N NaOH and extracted with ethyl acetate (2×30 mL). The ethyl acetate extracts were washed with pH 7 buffer (2×20 mL) and brine (30 mL), dried over Na2SO4, filtered, and evaporated to give the free base of the title compound (281 mg, 96%) as a colorless oil. Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H22CIN3O6S: 444.1 (M+H), 466.1 (M+Na). Found 444.6, 466.7.

1. stirringthe reaction was stirred at ambient temperature for 3 days
2. customN,N-Dimethylformamide was removed in vacuo
3. additionacetonitrile (1 mL) was added
4. customto precipitate excess 1H-pyrazole-1-carboxamidine hydrochloride
5. filtrationThe mixture was filtered
6. concentrationthe filtrate was concentrated in vacuo
7. customThe residual oil was partitioned between diethyl ether (20 mL) and water (20 mL)
8. washThe aqueous layer was washed with diethyl ether (2×20 mL)
9. extractionextracted with ethyl acetate (2×30 mL)
10. washThe ethyl acetate extracts were washed with pH 7 buffer (2×20 mL) and brine (30 mL)
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customevaporated