Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1846699Generated: November 2, 2026

Trifluoroacetic acid → 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-fluoro-4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamide

https://huagongshe.com/reaction/1846699

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantDiisopropylethylamineHCID 81531—
Reactant(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 1514389—
Reactant2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxamideHCID 57471883—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-fluoro-4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamideHCID 5747187843.3%

Reaction Steps

A solution of tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (0.30 M in NMP, 1.00 mL, 0.300 mmol) in NMP (1 mL) was added to 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxamide (12 mg, 0.027 mmol). DIEA (0.050 mL, 0.29 mmol) was also added. The mixture was stirred at 90 C for 1 h. After being cooled to room temperature, TFA (1 mL) was added. The solution was stirred at room temperature for 60 min. The mixture was purified by HPLC to give the titled compound (5 mg). MS 428.4 (M+H). UV λ=229.8, 313.8 nm.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952027B2
Source datasetuspto-grants-2015_02
ORD IDord-4988bac22dca472d8698fa3cfe51f7d9
Source noteuspto-grants-2015_02