D-Proline → 2-(4-Bromo-3-fluorophenyl)-7-(4-ethoxyphenoxy)imidazo[1,2-b][1,2,4]triazine
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH:9]=O)=[CH:5][CH:4]=1.N1CCC[C@@H:14]1C(O)=O.ClN1C(=O)CCC1=O.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[N:41]=[N:40][C:39]([NH2:42])=[N:38][CH:37]=2)=[CH:32][C:31]=1[F:43]>C(Cl)(Cl)Cl>[Br:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[N:38][C:39]3[N:40]([C:8]([O:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH2:1][CH3:14])=[CH:12][CH:11]=4)=[CH:9][N:42]=3)[N:41]=2)=[CH:32][C:31]=1[F:43]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled (0° C.) mixture of (4-methoxyphenoxy)acetaldehyde (33.2 mg, 0.2 mmol) and D-proline (4.6 mg, 0.04 mmol) in chloroform (1.0 mL) was added N-chlorosuccinimide (26.7 mg, 0.2 mmol) with stirring. The mixture was stirred at 0° C. for 30 min, then gradually warmed to ambient temperature for 2 h. To the reaction mixture was added 6-(4-bromo-3-fluorophenyl)-1,2,4-triazin-3-amine (26.9 mg, 0.1 mmol). The reaction mixture was stirred for 1 h and then the solvent was removed under reduced pressure. The residue was dissolved in isopropanol (2 mL) and heated to 100° C. overnight. After cooling, the mixture was filtered and the filtrate was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=415.0/416.9.
Workup
- temperatureTo a cooled
- stirringThe mixture was stirred at 0° C. for 30 min
- stirringThe reaction mixture was stirred for 1 h
- customthe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in isopropanol (2 mL)
- temperatureheated to 100° C. overnight
- temperatureAfter cooling
- filtrationthe mixture was filtered
- customthe filtrate was purified by RP-HPLC (pH 10)
Sources & evidence
- ORD record
- ord-fd2f9702dba042d9bf06fb42361ac3e2
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767675B2
Reaction notes
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