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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1697364Generated: October 27, 2026

Diisopropylethylamine → Methyl 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoate

https://huagongshe.com/reaction/1697364

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactantmethyl 3-(3,5-dibromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoateHCID 66688740—
Reactant1-[2-(Benzyloxy)phenyl]cyclobutan-1-amineHCID 66690033—
SolventWaterHCID 962—
SolventEthyl AcetateHCID 8857—
Solvent1,4-DioxaneHCID 31275—
ProductMethyl 3-(3-(1-(2-(benzyloxy)phenyl)cyclobutylamino)-5-bromo-2-oxopyrazin-1(2H)-yl)-4-methylbenzoateHCID 6668970994.3%

Reaction Conditions

Temperature100 °C

Reaction Steps

To 3-(3,5-dibromo-2-oxo-2H-pyrazin-1-yl)-4-methyl-benzoic acid, methyl ester (Example 1b, 1.083 g) in dioxane (6 mL) was added 1-(2-(benzyloxy)phenyl)cyclobutanamine (Example 268c, 1.16 g) and N,N-diisopropylethylamine (0.76 mL) and the reaction heated at 100° C. for 16 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and water, and the organic layer was separated, dried (MgSO4), filtered and the crude product purified (SiO2 chromatography eluting with 20-50% ethyl acetate in iso-hexane) to afford the subtitle product (1.46 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163905B2
Source datasetuspto-grants-2012_04
ORD IDord-f994e4e80e9a4af4af270b03177c34cb
Source noteuspto-grants-2012_04