Diisopropylethylamine → Tert-butyl 4-(5-(((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)carbamoyl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	6-(4-((Tert-butoxy)carbonyl)piperazin-1-yl)pyridine-3-carboxylic acid	HCID 2771823	—
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-Fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methanamine	HCID 67208645	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Tert-butyl 4-(5-(((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)carbamoyl)pyridin-2-yl)piperazine-1-carboxylate	HCID 86679720	—

Reaction Steps

To a mixture of (3-fluoro-2′-(trifluoromethyl)-[2,4′-bipyridin]-5-yl)methanamine 84-2 (53 mg, 0.195 mmol), 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)nicotinic acid 46-1 (16 mg, 0.195 mmol), and HATU (81.5 mg, 0.214 mmol) were added N,N-diisopropylethylamine (DIEA, 52 μL, 0.298 mmol) and DMF (1.0 mL). The solution was stirred overnight at room temperature and was subjected to silica gel column chromatography with 1:1 ethyl acetate/hexanes as eluent to give tert-butyl 4-(5-(((3-fluoro-2′-(trifluoromethyl)-[2,4′-bipyridin]-5-yl)methyl)carbamoyl)pyridin-2-yl)piperazine-1-carboxylate 46-2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181235B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-dec24e204a7a4d67bff263c7231afb07
Source note	uspto-grants-2015_11