Methylamine → N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Methylamine	HCID 6329	—
Reactant	2,1,3-Benzoxadiazole-5-carboxylic acid	HCID 2735454	—
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	N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide	HCID 59354764	79.2%

Reaction Steps

To a stirred solution of benzo[c][1,2,5]oxadiazole-5-carboxylic acid (0.49 g, 2.987 mmol) in DCM (50 mL) were added HATU (1.7 g , 4.481 mmol), N-methoxy, N-methylamine (0.44 g, 4.481 mmol) and TEA (914 mg, 8.963 mmol) at RT under a nitrogen atmosphere. The reaction mixture was then stirred at RT for 3 h, diluted with water and the aqueous layer was extracted with DCM (3×50 mL). The combined organic extracts were washed with water (50 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford N-methoxy-N-methylbenzo[c][1,2,5]oxadiazole-5-carboxamide (0.49 g, 79%) as a yellow oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09265767B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-2e3b8ff19c0a416abae8f20e81d44e38
Source note	uspto-grants-2016_02