4-Methylmorpholine → HCID 70098771, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Azetidine	HCID 10422	—
Reactant	3-Amino-6-methylpicolinic acid	HCID 572623	—
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	Tetrahydrofuran	HCID 8028	—
Product	HCID 70098771	HCID 70098771	65.5%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a stirred mixture of 3-amino-6-methylpicolinic acid (525 mg, 2.17 mmol) and azetidine (124 mg, 146 μl, 2.17 mmol) at r.t. in THF (15 ml) under an argon atmosphere were added HATU (1.65 g, 4.35 mmol) and 4-methylmorpholine (719 μl, 6.52 mmol). The mixture was heated to 70° C. overnight, then cooled to r.t. and concentrated. The crude product was purified by silica gel chromatography using a n-heptane/EtOAc gradient to give the title compound (272 mg, 65%) as off-white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08623866B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-64e5273824cf4e76a7c57ea0b551d7c5
Source note	uspto-grants-2014_01