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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 337142Generated: October 28, 2026

Hydrochloric Acid → N-Cyclopropyl-2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzamide

https://huagongshe.com/reaction/337142

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantCyclopropylamineHCID 69828—
Reactantmethyl 2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzoateHCID 66689715—
ReactantHCID 178418918HCID 178418918—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductN-Cyclopropyl-2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzamideHCID 66689387—

Reaction Steps

Isopropylmagnesium chloride (5.19 mL of a 2.0 M solution in THF) was added over 20 min of a solution of cyclopropylamine (1.830 mL) and methyl 2-fluoro-5-[3-{[1-(2-hydroxyphenyl)cyclopropyl]amino}-2-oxopyrazin-1(2H)-yl]-4-methylbenzoate (Example 318f, 1.063 g) in THF (20 mL) stirring at room temperature under nitrogen. The reaction mixture was stirred for 1 h. Water and 2 M HCl were cautiously added and the volatiles removed in vacuo. The residue was basified with saturated aqueous sodium bicarbonate solution and extracted into DCM. The organics were combined, dried (MgSO4) and evaporated to give the subtitle compound (1.189 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08889692B2
Source datasetuspto-grants-2014_11
ORD IDord-7e1b59b1453849ec8425104254c0563a
Source noteuspto-grants-2014_11