4-Methylmorpholine → HCID 178508424, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
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-Amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid	HCID 58442296	—
Reactant	HCID 178509226	HCID 178509226	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178508424	HCID 178508424	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture comprising 3-amino-6-bromo-5-trifluoromethyl-pyrazine-2-carboxylic acid (Intermediate 2) (0.320 g, 1.118 mmol), 3-aminopyrazolo[3,4-b]pyridine (0.150 g, 1.118 mmol) and HATU (0.425 g, 1.118 mmol) in DMF (5 ml) was treated with N-methylmorpholine (0.111 ml, 1.118 mmol) and stirred at 80° C. overnight. After cooling to RT, the mixture was diluted with water (25 ml) and the resulting yellow precipitate was filtered under vacuum and washed with water. The crude material was purified by chromatography on silica eluting with iso-hexane:EtOAc (gradient of 0 to 100 EtOAc) to give the title compound as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09056867B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-aee5272df73e4ab980de3208a4dc50db
Source note	uspto-grants-2015_06