Dimethylformamide → 2-[4-(4-Amino-quinazolin-7-ylmethyl)-3-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

1,8-Diazabicyclo[5.4.0]undec-7-ene (37 mg, 0.24 mmol) is added to a suspension containing (3-{3-[4-(4-amino-quinazolin-7-ylmethyl)-3-oxo-piperazin-1-yl]-prop-1-ynyl}-pyridin-4-yl)-carbamic acid tert-butyl ester (59 mg, 0.12 mmol) in anhydrous CH3CN (5 mL) and the mixture is warmed to 50° C. Dimethylformamide (1 mL) is added to solubilize and the homogeneous solution is maintained for 5 h at 50° C. The reaction mixture is diluted with EtOAc (50 mL) and water (50 mL) and the layers are separated. The aqueous layer is extracted twice with EtOAc (25 mL) and the combined organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to provide 50 mg of the product as a crude solid which is used directly without further purification. 1H NMR (300 MHz, CDCl3) δ1.64 (s, 9H), 2.78 (m, 2H), 3.30 (m, 2H), 3.37 (s, 2H), 3.95 (s, 2H), 4.74 (s, 2H), 6.24 (br s, 2H), 6.63 (s, 1H), 7.40 (dd, J=8.5, 1.6 Hz, 1H), 7.64 (s, 1H), 7.81 (d, J=5.8 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.99 (s, 1H), 8.39 (d, J=5.8 Hz, 1H), 8.58 (s, 1H), 8.77 (s, 1H) ppm.

Provenance & Evidence