Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 11651576, compound

Participants

Role	Name	HCID	Charge
Reactant	Methanamine, N-methoxy-, hydrochloride (1:1)	HCID 81138	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Pyridinecarboxylic acid, 4-(trifluoromethyl)-	HCID 2777549	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 11651576	HCID 11651576	—

Reaction Steps

To a solution of 4-(trifluoromethyl)nicotinic acid (2.11 g, 11.04 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.077 g, 11.04 mmol) in DCM (20 mL) was added N-ethyl-N-isopropylpropan-2-amine (3.78 mL, 22.08 mmol), and HATU (4.20 g, 11.04 mmol). The reaction was stirred at rt under N2 for 5 h. The reaction was then diluted with H2O (50 mL) and extracted with DCM (2×50 mL). The organic layers were combined, dried (MgSO4), and concentrated to give the amide. Purification by ISCO (80 g SiO2, 10-50% EtOAc/hexanes) gives N-methoxy-N-methyl-4-(trifluoromethyl)nicotinamide as a yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08710043B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-f85fe88618f54604b136b782b5ece97f
Source note	uspto-grants-2014_04