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. 2014 Dec 4;57(24):10544–10550. doi: 10.1021/jm501527z

Scheme 3. Synthesis of 4-Oxo-[1]benzopyrano[4,3-c]pyrazole Analogue 8ln (Method C).

Scheme 3

Reagents and conditions: (a) 21 (4-Cl-3-OMePhNHMe) or 2k (4-Cl-3-OMePhNH2), K2CO3, CH2Cl2, 0 °C to rt; (b) for 4l, t-butyl carbazate, K2CO3, KI, acetone, 65 °C, 18 h or for 4m, t-butyl carbazate, DIPEA, toluene 105 °C, 16 h; (c) TFA in CH2Cl2 (1:4), 2 h, then 7a (or 4-chloro-3-formyl-7-methylcoumarin, 7b), AcOH (cat.), EtOH, 105 °C, 20 min.