Sodium cyanoborohydride → 4-[2-(4-{[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]amino}piperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Sodium cyanoborohydride	HCID 5003444	—
Reactant	4-[2-(4-aminopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile	HCID 66774987	—
Reactant	(2E)-3-(2,5-difluorophenyl)-2-propenal	HCID 86642138	—
Solvent	Dichloromethane methanol	HCID 21226129	—
Product	4-[2-(4-{[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]amino}piperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile	HCID 11983216	30.9%

Reaction Steps

4-[2-(4-Aminopiperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Intermediate 58) (1.5 mmol), (2E)-3-(2,5-difluorophenyl)acrylaldehyde (202 mg, 1.2 mmol) (FR 2872164) (200 mg, 1.1 mmol) and sodium cyanoborohydride were reacted as described under Example 21. Chromatography on silica gel with dichloromethane/methanol gave 168 mg (25%) product

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08124602B2
Source dataset	uspto-grants-2012_02
ORD ID	ord-f85bccb0435d4d868ae70547a876e9f6
Source note	uspto-grants-2012_02