Sodium cyanoborohydride → 4-(2-{4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-6-fluoro-2H-1,4-benzoxazin-3(4H)-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium cyanoborohydride	HCID 5003444	—
Reactant	2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde	HCID 21873668	—
Reactant	4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-fluoro-2H-1,4-benzoxazin-3(4H)-one	HCID 66774353	—
Product	4-(2-{4-[(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-6-fluoro-2H-1,4-benzoxazin-3(4H)-one	HCID 15983554	32.3%

Reaction Steps

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-fluoro-2H-1,4-benzoxazin-3(4H)-one (Intermediate 54) (0.7 mmol), 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (WO 2004/058144) (140 mg, 0.84 mmol), and sodium cyanoborohydride (90 mg, 1.4 mmol) were reacted as described under Example 21 to give 100 mg (32%) product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08124602B2
Source dataset	uspto-grants-2012_02
ORD ID	ord-e1d76f8dd1c048f5ac8fde3e34df2cf2
Source note	uspto-grants-2012_02