Diisopropylethylamine → 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-N-(3-trifluoromethyl-1,2,4-oxadiazol-5-ylmethyl)-nicotinamide

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	(3-(Trifluoromethyl)-1,2,4-oxadiazol-5-YL)methanamine	HCID 55263061	—
Reactant	5-Cyclopentyl-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid	HCID 71294186	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-N-(3-trifluoromethyl-1,2,4-oxadiazol-5-ylmethyl)-nicotinamide	HCID 71509310	38.7%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid (Example 9c) (124 mg, 0.43 mmol) in DMF (4 mL) were added DIPEA (0.1 mL, 1.08 mmol) and HATU (204 mg, 0.54 mmol) at 25° C. The reaction mixture was stirred for 30 min at 25° C. To this was added C-(3-trifluoromethyl-1,2,4-oxadiazol-5-yl)-methylamine (CAN 944905-93-5) (60 mg, 0.36 mmol) and the reaction mixture was stirred for 12 h at 25° C. Volatiles were removed in vacuo and the resultant residue was purified by prep-HPLC to get 5-cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-N-(3-trifluoromethyl-1,2,4-oxadiazol-5-ylmethyl)-nicotinamide (61 mg, 38.7%) as off-white solid; MS (ESI): 439 (M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08629166B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-7051744875464644a3b792dddfc6fc2c
Source note	uspto-grants-2014_01