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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1880277Generated: November 1, 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/1880277

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 numberUS08318755B2
Source datasetuspto-grants-2012_11
ORD IDord-d7d248e4b3bd409bbe7640a7f187948b
Source noteuspto-grants-2012_11