Diisopropylethylamine → HCID 67208646, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Fluoroisonicotinic acid	HCID 345360	—
Reactant	Tert-butyl (piperidin-4-ylmethyl)carbamate	HCID 723429	—
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	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 67208646	HCID 67208646	—

Reaction Steps

To a mixture of tert-butyl piperidin-4-ylmethylcarbamate 93-1 (1.07 g, 5.0 mmol), 2-fluoroisonicotinic acid 93-2 (706 mg, 5.0 mmol) and HATU (1.90 g, 5.0 mmol) in DMF (20 mL) was added DIEA (2.5 mL, 15.0 mmol) at room temperature. The mixture was stirred for 2 hours. The mixture was diluted with ethyl acetate (100 mL), washed with H2O and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 5% methanol in dichloromethane to give tert-butyl (1-(2-fluoroisonicotinoyl)piperidin-4-yl)methylcarbamate 93-3 as a pale yellow solid. MS m/z 338.1 (M+1)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181235B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-f7d9bb31907a417b85418bd8b82c5c4b
Source note	uspto-grants-2015_11