Diisopropylethylamine → 5-Methyl-oxazole-4-carboxylic acid [5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-amide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	5-methyl-1,3-oxazole-4-carboxylic Acid	HCID 11355484	—
Reactant	5-Cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine	HCID 71294172	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-Methyl-oxazole-4-carboxylic acid [5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-amide	HCID 71509593	21.4%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 5-methyl-4-oxazolecarboxylic acid (CAN 103879-58-9) (73 mg, 0.57 mmol) in DMF (4 mL) were added DIPEA (0.1 mL, 1.15 mmol) and HATU (219 mg, 0.57 mmol) at 25° C. The reaction mixture was stirred for 30 min at 25° C. Then, 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine (Example 1c) (100 mg, 0.38 mmol) was added and the reaction mixture was stirred at 25° C. for 12 h. Volatiles were removed in vacuo and the resultant residue was purified by prep-HPLC to get the title compound (30 mg, 21.3%) as off-white solid. MS (ESI): 370 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08455501B2
Source dataset	uspto-grants-2013_06
ORD ID	ord-b3d72266df3148e6b8160523c197df41
Source note	uspto-grants-2013_06