D-Proline → 2-(4-Bromo-3-fluorophenyl)-7-[(4-methoxyphenyl)thio]imidazo[1,2-b][1,2,4]triazine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH:11]=O)=[CH:5][CH:4]=1.N1CCC[C@@H]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:10]([S:9][C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)=[CH:11][N:42]=3)[N:41]=2)=[CH:32][C:31]=1[F:43]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) reaction mixture of [(4-methoxyphenyl)thio]acetaldehyde (36.4 mg, 0.2 mmol) and D-proline (4.6 mg, 0.04 mmol) in chloroform (1.2 mL) was added N-chlorosuccinimide. (26.7 mg, 0.2 mmol). The reaction mixture was stirred at 0° C. for 30 min, then gradually warmed to RT 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. The solvent was removed under reduced pressure. The residue was dissolved in isopropanol (2 mL) and heated at 100° C. overnight. After cooling, the reaction mixture was filtered and the filtrate was purified by RP-HPLC (pH=10) to afford the desired product. LCMS: (M+H)+=431.0.
Workup
- temperatureTo a cooled
- temperaturegradually warmed to RT for 2 h
- stirringThe reaction mixture was stirred for 1 h
- customThe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in isopropanol (2 mL)
- temperatureheated at 100° C. overnight
- temperatureAfter cooling
- filtrationthe reaction mixture was filtered
- customthe filtrate was purified by RP-HPLC (pH=10)
Sources & evidence
- ORD record
- ord-6f5357e382584a1fb4f5669b0aa7f1f2
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767675B2
Reaction notes
Loading…