4-Methylmorpholine → 4-fluoro-N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	4-Fluorobenzoic Acid	HCID 9973	—
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	7-Methoxy-4-(tetrahydro-pyran-4-yl)thiazolo[5,4-c]pyridin-2-ylamine	HCID 86038492	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4-fluoro-N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide	HCID 86597279	75.7%

Reaction Steps

To a stirred solution of 42 mg (0.30 mmol) 4-fluoro-benzoic acid in 4 ml THF were added 126 mg (0.33 mmol) HATU and 0.066 ml (0.60 mmol) N-methylmorpholine and stirring continued at 50° C. for 6 h. 40 mg (0.15 mmol) 7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-ylamine was then added and stirring continued at 50° C. for 16 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) followed by trituration in ether afforded 44 mg (75%) 4-fluoro-N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide as a white crystalline solid. ES-MS m/e (%): 388 (M+H+, 100).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07273865B2
Source dataset	uspto-grants-2007_09
ORD ID	ord-96b039fc21eb4288a01bfa0a068f090a
Source note	uspto-grants-2007_09