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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 930290Generated: October 28, 2026

5-chloro-N-((4S,6S)-4-(5-(5-chloropicolinamido)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)picolinamide → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamide

https://huagongshe.com/reaction/930290

Reaction equation

Participants

RoleNameHCIDCharge
Reactant5-chloro-N-((4S,6S)-4-(5-(5-chloropicolinamido)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)picolinamideHCID 86732121—
SolventAmmonia methanolHCID 21705897—
ProductN-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-chloropicolinamideHCID 7166746174.7%

Reaction Steps

A solution of 5-chloro-N-((4S,6S)-4-(5-(5-chloropicolinamido)-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)picolinamide (4k 85.3 mg, 0.150 mmol) in 2 M NH3/MeOH (Aldrich; 4.0 mL) was heated to 50° C. for 16 h. The solution was concentrated and purified by flash chromatography on silica gel (Gradient: 20%→100% EtOAc/hexane) to give the title compound (48.2 mg, 0.112 mmol) as a white solid. MS m/z=431.0, [M+H]+. Calculated for C18H15ClF4N4O2: 430.8

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09296734B2
Source datasetuspto-grants-2016_03
ORD IDord-bfae3ee654f849ba8f9c1f3cf3a1964d
Source noteuspto-grants-2016_03