HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-fluoro-4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected | HCID 1514389 | — |
| Reactant | 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(thiazol-4-yl)phenylamino)pyrimidine-5-carboxamide | HCID 57471883 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-[3-fluoro-4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamide | HCID 57471878 | 43.3% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08349860B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-be15d7da394f4e7787ea67f408d4871d |
| Source note | uspto-grants-2013_01 |