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. 2014 Feb 8;5(4):416–421. doi: 10.1021/ml4005232

Scheme 1. Chemical synthesis of AZD3199.

Scheme 1

Reagents and conditions: (a) 18 + (COCl)2 (1.1 mol equiv), dimethyl formamide (cat.), CH2Cl2, rt, 15 h, concentrate and add to 17, Hunig’s base (2 mol equiv), CH2Cl2, rt, 20 h (75%). (b) (i) dimethyl sulfoxide (2.2 mol equiv), CH2Cl2, −78 °C, add (COCl)2 (1.1 mol equiv), stir 15 min; (ii) add 19, stir 15 min; (iii) add triethylamine (5 mol equiv) and warm to rt 90 min; (iv) 20 in CH2Cl2, sodium triacetoxyborohydride (2 mol equiv), rt (27%).