Triethylamine → 3-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride	HCID 2734059	—
Reactant	N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride	HCID 21097525	—
Reactant	3-(6-Chloropyridin-3-yl)prop-2-enoic acid	HCID 53425056	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamide	HCID 72335662	96%

Reaction Steps

3-Fluoro-4-methanesulfonylaminobenzylamine hydrochloride (51 mg, 0.201 mmol) was suspended in THF and treated with triethylamine (23 mg, 0.22 mmol) and then the resulting mixture was stirred for 10 mins. 3-(6-chloro-pyridin-3-yl)-acrylic acid (37 mg, 0.201 mmol) was added to the reaction mixture followed by DMTMM (61 mg, 0.22 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat'd NaHCO3 (×2), brine, and then dried over anhyd. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was column-chromatographed to yield the title compound (74 mg, 96%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07858621B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-ca373f953f734803a6b9322ee87447c3
Source note	uspto-grants-2010_12