Acetic Acid → HCID 178481265, compound

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium triacetoxyborohydride	HCID 5049666	—
Reactant	4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzaldehyde	HCID 59472892	—
Reactant	2-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride	HCID 178478534	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 178481265	HCID 178481265	—

Reaction Steps

To a stirred solution of 13-2 (0.5 g, 1.2 mMol) and 8-5 (0.34 g, 1.3 mMol) in NMP (10 mL) was added triethylamine (0.33 mL, 2.3 mMol) followed by acetic acid (0.13 mL, 2.3 mMol). After stirring overnight at room temperature, sodium triacetoxyborohydride (0.3 g, 1.3 mMol) was added in portions. After stirring for 6 hours, the solution was filtered through a syringe filter and purified on a C18 reverse phase HPLC to give 13-3 as a solid. Mass (M+1) calculated: 644.2993 observed: 644.2988

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08008317B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-feda09550a7e4fe69e5c1e3a4b30dd44
Source note	uspto-grants-2011_08