N-methyl-2-pyrrolidone → 2-phenyl-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-propionamide

Participants

Role	Name	HCID	Charge
Reactant	N-methyl-2-pyrrolidone	HCID 13387	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-ylamine	HCID 118061715	—
Product	2-phenyl-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-propionamide	HCID 72544214	—

Reaction Steps

4-(Toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-ylamine (20 mg, 0.065 mmol) was dissolved in N-methylpyrrolidinone (0.5 mL), followed by (d,l)-2-phenylpropionic acid (30 μL, 0.11 mmol), HATU (45 mg, 0.12 mmol), and diisopropyl ethylamine (23 μL, 0.13 mmol). The reaction mixture was stirred at room temperature for 18 hours. Then, the reaction mixture was then purified by HPLC to give 2-phenyl-N-[4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl]-propionamide. LCMS (ESI): calc. C23H23N3O4S=437; obs. M+H=438.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09394315B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-f03919e9bec84b98808144c981959c4d
Source note	uspto-grants-2016_07