3-Aminopyridine → 5-[(Dimethylamino)sulfonyl]-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Temperature

25 °C

A solution of oxalyl chloride (0.06 ml, 0.69 mmol) in dichloromethane (5 ml) was added dropwise over 1 minute to a stirred solution of 5-[(dimethylamino)sulfonyl]-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 63; 230 mg, 0.69 mmol) in dichloromethane (5 ml) at 0° C. The reaction mixture was stirred at 25° C. for 0.5 h, and then concentrated under reduced pressure to give the crude acyl chloride as a yellow solid. A solution of this crude acyl chloride in dichloromethane (5 ml) was added dropwise over 5 min to a stirred solution of 3-pyridinamine (64.5 mg, 0.69 mmol) and diisopropylethylamine (0.12 ml, 0.69 mmol) in dichloromethane (20 ml) under nitrogen at 0° C. The reaction mixture was stirred at 25° C. for 1 h. The organic phase was washed with water (25 ml) three times and saturated brine (10 mL) two times, dried over sodium sulfate, and evaporated in vacuo to give the crude product as a orange oil. The product was crystallized from methanol to yield the title compound as a white solid. 170 mg.

1. concentrationconcentrated under reduced pressure
2. customto give the crude acyl chloride as a yellow solid
3. stirringThe reaction mixture was stirred at 25° C. for 1 h
4. washThe organic phase was washed with water (25 ml) three times and saturated brine (10 mL) two times
5. dry with materialdried over sodium sulfate
6. customevaporated in vacuo
7. customto give the crude product as a orange oil
8. customThe product was crystallized from methanol

ORD record

ord-96eb3301d376423889f334b8d97e74ed

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778939B2