Acetic Acid → HCID 178478337, compound

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Sodium triacetoxyborohydride	HCID 5049666	—
Reactant	4-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehyde	HCID 57500732	—
Reactant	2-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride	HCID 178478534	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 178478337	HCID 178478337	—

Reaction Steps

To a stirred solution of 9-1 (4.9 g, 14.2 mMol) and 8-5 (4.2 g, 15.6 mMol) in NMP (50 mL) was added triethylamine (6 mL, 42.6 mMol) followed by acetic acid (1.6 mL, 28.4 mMol). After stirring at ambient temperature overnight, sodium triacetoxyborohydride (3.6 g, 17 mMol) was added in portions. Upon completion, the reaction was diluted with ethyl acetate and washed with saturated NaHCO3, followed by water, then brine. The organic layer was dried with Na2SO4 and MgSO4, filtered and concentrated in vacuo. The crude residue purified using flash chromatography on silica (gradient: 0% to 10% MeOH in CHCl3 over 25 min) to yield 9-2 as an orange solid. LC/MS (M+1) calculated: 559.1; observed: 559.2

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08008317B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-46d5555773404055a69342c57682b8c5
Source note	uspto-grants-2011_08