Trifluoroacetic acid → 3-(7-Amino-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-(2-cyclopropylethyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one

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Reaction Steps

A solution of Example 157F (1.06 g, 2.00 mmol) in dichloromethane (10 mL) was treated with trifluoroacetic acid (10 mL) at room temperature for 1 hour. After concentrating in. vacuo, the resulting oil was partitioned between ethyl acetate and aqueous NaHCO3, the organic layer was removed and the aqueous layer extracted 3 times with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in. vacuo to yield a solid that was used without further purification. 1H NMR (300 MHz, DMSO-d6): δ ppm−0.25 (m, 2H) 0.25 (m, 2H) 0.46 (m, 2H) 0.80 (m, 1H) 1.57 (s, 3H) 2.15 (m, 1H) 2.32 (m, 1H) 6.99 (m, 2H) 7.44 (d, J=8.82 Hz, 1H) 7.54 (m, 1H) 7.77 (d, J=4.04 Hz, 2H) 8.15 (d, J=7.72 Hz, 1H) 13.55 (s, 1H). MS (ESI+) m/z=438 (M+H)+, 455 (M+NH4)+.

Provenance & Evidence