Triethylamine → N-{4-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]butyl}isoxazole-3-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	3-Isoxazolecarboxylic acid	HCID 11286453	—
Reactant	5-(4-Aminobutyl)-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one	HCID 71136776	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-{4-[1-(2,2-Dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo-[4,5-b]pyridin-5-yl]butyl}isoxazole-3-carboxamide	HCID 71136780	—

Reaction Steps

To a stirred solution of 3-isoxazolecarboxylic acid (0.02 g, 0.18 mmol), and triethylamine (0.1 mL, 0.72 mmol) in dichloromethane (2 mL) was added HATU (0.07 g, 0.18 mmol). The resulting mixture was stirred 20 minutes. To this mixture was added 38-2 (0.04 g, 0.14 mmol) and the resulting mixture was stirred room temperature overnight. The mixture was washed with water and concentrated. Flash column separation using a 10-70% ethyl acetate/hexane gradient gave 38-3. (0.045 g, 85%). HRMS (M+H)+: observed=386.2188, calculated=386.2187

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09315518B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-6c54fdecc69c4d66908976e7e64a0fec
Source note	uspto-grants-2016_04