N-{3-[3-(2-{[3-(1,3-Oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide → N-{3-[3-(2-{[3-({[2-(Dimethylamino)ethyl]amino}methyl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A suspension of N-[(3-aminophenyl)methyl]-N-[2-(dimethylamino)ethyl]-2,2,2-trifluoroacetamide (61 mg, 0.21 mmol) and N-{3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide (75 mg, 0.17 mmol) (see Example 2, Step B) in i-PrOH (3 mL) was acidified with 3 drops of 12 N HCl and heated in a microwave for 25 min. at 180° C. The reaction mixture was then diluted with DCM, washed with 2 N NaOH, dried over Na2SO4, and adsorbed onto silica gel. The crude product was purified by column chromatography to generate the title compound in 66% yield. 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=6.8 Hz, 1H), 8.36 (d, J=8.8 Hz, 1H), 8.16 (d, J=5.1 Hz, 1H), 7.80 (d, J=7.2 Hz, 1H), 7.73 (s, 1H), 7.53-7.61 (m, 3H), 7.32-7.45 (m, 4H), 7.01 (s, 2H), 6.90 (t, J=6.6 Hz, 1H), 6.55 (d, J=5.1 Hz, 1H), 3.94 (s, 2H), 3.79 (s, 2H), 2.70 (t, J=5.8 Hz, 2H), 2.42 (t, J=5.9 Hz, 2H), 2.18 (s, 6H). ES-LC/MS m/z=603 [M+H]+.

Provenance & Evidence