Sodium cyanoborohydride → 3-Oxo-4-[2-(6-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)ethyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Sodium cyanoborohydride	HCID 5003444	—
Reactant	3-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde	HCID 21873737	—
Reactant	4-[2-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile	HCID 66775360	—
Product	3-Oxo-4-[2-(6-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-3-azabicyclo[3.1.0]hex-3-yl)ethyl]-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile	HCID 15982017	6%

Reaction Steps

4-[2-(6-Amino-3-azabicyclo[3.1.0]hex-3-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Intermediate 93), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehyde (WO 2004/058144) and sodium cyanoborohydride were reacted as described under Example 21 to give the product as an off-white solid in 6% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07875715B2
Source dataset	uspto-grants-2011_01
ORD ID	ord-6e1ba7db342f42d691518c8d5ec7804e
Source note	uspto-grants-2011_01