Hydrochloric Acid → HCID 75068495, compound

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	N,O-Dimethylhydroxylamine	HCID 14232	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-Boc-2-Piperidineacetic Acid	HCID 5058536	—
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	—
Product	HCID 75068495	HCID 75068495	90.8%

Reaction Steps

A solution of 2-carboxymethyl-piperidine-1-carboxylic acid tert-butyl ester (Beckett et al, J. Med. Chem., 563,1969) (2.29 g, 10 mmol) in DMF (20 ml) was treated sequentially with N,N-diisopropylethylamine (4.0 ml), HATU (3.8 g, 10 mmol) and O,N-dimethyl-hydroxylamine.HCl (0.98 g, 10 mmol). The reaction mixture was stirred under argon at room temperature for 16 h. The volatiles were removed in vacuo and the residue was chromatographed (silica gel, diethyl ether) to afford the title compound as a white solid (2.60 g, 90%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07470710B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-c54caa9639814a5c9f1e1673069df189
Source note	uspto-grants-2008_12