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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 526937Generated: October 30, 2026

Trifluoroacetic acid → N-((trans-2-aminocyclohexyl)methyl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amine

https://huagongshe.com/reaction/526937

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactanttert-butyl trans-2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexylcarbamateHCID 68007592—
SolventDichloromethaneHCID 6344—
ProductN-((trans-2-aminocyclohexyl)methyl)-2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-amineHCID 68007392—

Reaction Steps

A solution of the tert-butyl trans-2-((2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)methyl)cyclohexylcarbamate, 14e, (0.52 g) in CH2Cl2 (5 mL) was treated with TFA (2.5 mL) for 30 min. the solution was concentrated in vacuo and the resulting crude material was taken up in CH3CN and concentrated in vacuo several times to remove excess TFA and to provide the desired amine, 14f, as racemic mixture of trans isomers, as the TFA salt, which was sufficiently pure for use in the next reaction.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09345708B2
Source datasetuspto-grants-2016_05
ORD IDord-b82b43e0223345d7a76c47f52628d3ea
Source noteuspto-grants-2016_05