Diisopropylethylamine → Tert-butyl [({3-[4-(2-cyclopropylethyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4h-1,2,4-benzothiadiazin-7-yl}amino)sulfonyl]acetate

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Reaction Steps

To a stirring solution of Example 158 (0.070 g, 0.160 mmol) in dichloromethane containing N,N-diisopropylethylamine (0.036 mL, 0.208 mmol) was added chlorosulfonyl-acetic acid tert-butyl ester (0.041 g, 0.192 mmol). The reaction mixture was stirred overnight and then partitioned between ethyl acetate and water. The organic layer was washed sequentially with 10% 1N HCl in water, bicarb, and brine. The product was purified by flash chromatography on SiO2 eluting with 0-50% ethyl acetate/hexanes yielding the title compound (0.030 g, 30.5% yield) as a light yellow solid. 1H NMR (300 MHz, DMSO-d6): δ ppm−0.23 (dd, J=9.01, 4.23 Hz, 2H) 0.25 (d, J=6.62 Hz, 2H) 0.45 (m, 2H) 0.85 (m, 1H) 1.25 (m, 1H) 1.39 (s, 9H) 1.57 (m, 3H) 2.34 (m, 1H) 4.22 (m, 2H) 7.55 (m, 2H) 7.62 (dd, J=10.29, 2.21 Hz, 2H) 7.75 (m, 3H) 8.15 (d, J=7.72 Hz, 1H) 10.61 (s, 1H) 13.73 (m, 1H). MS (ESI+) m/z=516 (M+H)+.

Provenance & Evidence