Réaction #91336

Équation de réaction

solution

3-[(4-chloro-2-cyclopropylbenzyl)amino]pyridine-4-carboxylic acid

thionyl chloride

MeOH

→

title compound

Rendement 31.0%

methyl 3-[(4-chloro-2-cyclopropylbenzyl)amino]pyridine-4-carboxylate

Rendement 31.0%

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 2 days
2. 2
   ConcentrationThe solution was concentrated
3. 3
   Autrepurified by prep-HPLC

Mode opératoire

To a solution of Example 26 (15 mg, 0.05 mmol) in MeOH (10 mL) was added thionyl chloride (1 mL) at rt. The reaction was stirred at reflux for 2 days. The solution was concentrated and purified by prep-HPLC to give 5 mg (31%) of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ 0.70-0.73 (2H, m), 1.0-1.04 (2H, m), 2.0-2.04 (1H, m), 3.96 (2H, s), 4.74 (3H, s), 7.08 (1H, d, J=1.6 Hz), 7.14 (1H, dd, J=2.0, 8.4 Hz), 7.25 (1H, d, J=8.0 Hz), 7.91 (1H, d, J=4.0 Hz), 8.05 (1H, d, J=5.6 Hz), 8.13 (1H, s). [M+H] Calc'd for C17H17ClN2O2, 317. found, 317.

Source