3-Aminopyridine → HCID 11560023, compound

Participants

Reaction Steps

A solution of 5-bromo-2-methyl-thiazole-4-carboxylic (prepared as described in example 119, steps A to B) (0.13 g, 0.60 mmol) in dichloromethane (5.00 ml) and DMF (0.10 ml) was treated with thionyl chloride (0.08 g, 0.66 mmol) and stirred at room temperature for 4.5 h. After this time, 6-amino-pyridin-2-ylmethyl ester (0.10 g, 0.60 mmol) and DIPEA (0.16 g, 1.20 mmol) were added, and the mixture stirred for 30 min. The solvents were then evaporated and the residue purified by flash chromatography (heptane/ethyl acetate) to yield acetic acid 6-[(5-bromo-2-methyl-thiazole-4-carbonyl)-amino]-pyridin-2-ylmethyl ester (0.17 g, 76%) as a white solid, MS (ISP): m/e=372.0, 370.0 (M+H+). Acetic acid 6-[(5-bromo-2-methyl-thiazole-4-carbonyl)-amino]-pyridin-2-ylmethyl ester was then coupled with pyridin-3-ylamine in step B to yield the title compound.

Provenance & Evidence