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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 337173Generated: October 29, 2026

Dichloromethane → N-(sec-butyl)-4-chloro-3-[3-{(1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide

https://huagongshe.com/reaction/337173

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantBoron tribromideHCID 25134—
Reactant3-[3-({1-[2-(Benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chloro-N-cyclopropylbenzamideHCID 66689500—
SolventWaterHCID 962—
ProductN-(sec-butyl)-4-chloro-3-[3-{(1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamideHCID 66689180—

Reaction Conditions

Temperature0 °C

Reaction Steps

A solution of 3-[3-({1-[2-(benzyloxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-4-chloro-N-cyclopropylbenzamide (Example 330g, 2.23 g) dissolved in DCM (30 mL) was treated with boron tribromide (8.43 mL of a 1M solution in DCM) at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. for 1 h. The reaction mixture was diluted with water (200 mL), and extracted with dichloromethane (250 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was triturated with diethyl ether (50 mL) to afford the subtitle compound (1.760 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08889692B2
Source datasetuspto-grants-2014_11
ORD IDord-f17b71feab764badbf043d980742ccff
Source noteuspto-grants-2014_11