Chloroacetamide → 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)acetamide

Participants

Reaction Steps

Using similar reaction conditions as described in step-i of example-82A, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 1 compound of example 137) (100 mg, 0.164 mmol) was alkylated using 2-chloroacetamide (23 mg, 0.247 mmol), sodium bicarbonate (42 mg, 0.494 mmol) and ethanol/acetone (3/3 mL) to get 80 mg (73.0%) of the titled compound after purification by column (Silica gel 60/120) chromatography using 5% methanol in dichloromethane as eluent. 1H NMR (CDCl3, 300 MHz): δ 8.60-8.06 (d, 1H), 8.40-8.39 (d, 1H), 8.11-8.08 (d, 2H), 8.00-7.99 (d, 2H), 7.85 (s, 1H), 7.80 (s, 1H), 7.71-7.67 (m, 2H), 7.37-7.33 (m, 2H), 7.06-6.90 (m, 3H), 7.76-7.73 (d, 1H), 5.45 (s, 1H), 5.37 (s, 2H), 3.65-3.62 (t, 4H), 3.09 (s, 1H), 2.71-2.68 (t, 4H), 2.37 (s, 3H).

Provenance & Evidence