Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2401235Generated: November 2, 2026

Hydrochloric Acid → HCID 70944636, compound

https://huagongshe.com/reaction/2401235

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantDiethyl EtherHCID 3283—
ReactantDiisopropylethylamineHCID 81531—
Reactant1H-Pyrrolo[2,3-b]pyridine-5-methanamine, 2-(trifluoromethyl)-HCID 67111459—
ReactantHCID 83854099HCID 83854099—
SolventEthyl AcetateHCID 8857—
SolventN-methyl-2-pyrrolidoneHCID 13387—
ProductHCID 70944636HCID 7094463612.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

1-[2-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methanamine (Intermediate 5, 100 mg, 0.465 mmol), 4-chloro-6-(1-fluoroethyl)-5-methylpyrimidine (Intermediate 45, 153 mg, 0.874 mmol) and DIPEA (0.162 mL, 0.929 mmol) were added together in N-methyl-2-pyrrolidone (NMP) (3 mL) and the resulting mixture was heated at 100° C. for 2 hours and allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4, 25+M) eluting with a gradient of 0-100% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure. The residue (26 mg) was dissolved in methanol (2 mL), treated with 1M HCl in diethyl ether (0.1 mL, 0.100 mmol) and the resulting mixture was evaporated under reduced pressure. The resulting solid was dried under high vacuum at 40° C. for 18 hours to give the title compound as a white solid (23 mg);

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08796283B2
Source datasetuspto-grants-2014_08
ORD IDord-db1eadcbca0c471497cba36cee2d0dfd
Source noteuspto-grants-2014_08