Trifluoroacetic acid → 4-(Cyclopropylamino)-2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5] triazine-8-carbaldehyde
Reaction equation
[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][CH:20]=[C:16]3[N:15]=[C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:30])[F:29])[CH:22]=3)[N:13]=2)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.FC(F)(F)[C:34](O)=[O:35]>ClCCl>[CH:1]1([NH:4][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:34]=[O:35])=[C:16]3[N:15]=[C:14]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:29])([F:30])[F:31])[CH:22]=3)[N:13]=2)[CH2:2][CH2:3]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate was dissolved in dichloromethane (0.7 mL) and trifluoroacetic acid (0.7 mL). After 1 h, the solution was concentrated under a stream of air to give crude 4-(cyclopropylamino)-2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5] triazine-8-carbaldehyde which was used without further purification. LCMS (ES): >90% pure, m/z 336 [M+1]+. 4-(cyclopropylamino)-2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazine-8-carbaldehyde (87 mg, 0.26 mmol) was dissolved in DMF (0.8 mL). Phosphorus(V) oxychloride (318 μL, 3.47 mmol) was added was added dropwise and the reaction was heated to 70° C. After 6 h, the solution was added dropwise to 6M NaOH (˜10 mL) cooled to 0° C. The pH was adjusted to 7 by the addition of 12N HCl. The precipitate was filtered off and dried in vacuo to furnish 4-(cyclopropylamino)-2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazine-8-carbaldehyde (71 mg, 75%) as a tan solid. LCMS (ES): >95% pure, m/z 364 [M+1]+.
Workup
- concentrationthe solution was concentrated under a stream of air
Sources & evidence
- ORD record
- ord-efa166f8aa0247eba0ed36e2b2565dbe
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575177B2
Reaction notes
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