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Stage #1: PF-04691502; 4-Nitrophenyl chloroformate In dichloromethane at 20℃;
Stage #2: C26H31N5O3 With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;
Synthesis of Compound 11
A vial was charged with (4-nitrophenyl) carbonochloridate (5.7 mg, 28 umol) and dichloromethane (0.5 mL). PF-04691502 (10 mg, 23.5 umol) was charged in a vial and dissolved in dichloromethane (0.5 mL). PF-04691502 solution was added to (4-nitrophenyl) carbonochloridate solution. After stirring at room temperature overnight, solvent was evaporated, then 0.5 mL DMF was added. 1A (16.3 mg, 35 umol) was charged in a vial and suspended in DMF (0.5 mL). Carbamate solution was added, followed by diisopropylethylamine (9.1 mg, 71 umol, 12 uL). Solution was stirred at room temperature overnight. Crude was purified by preparative FIPLC (40- 95% MeCN/water, 0.1% acetic acid). Pure fractions were pooled, frozen and lyophilized. 3 mg (14%) of white lyophilized powder was obtained (4.56 mins, M+H = 914).
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