Trifluoroacetic acid → 5-Bromo-3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]pyrazin-2-amine
Reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[N:10]=[C:11]([C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][Cl:42])=[CH:37][CH:36]=3)[CH:31]=2)[C:12]([N:15](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:13][CH:14]=1>ClCCl>[Br:8][C:9]1[N:10]=[C:11]([C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][Cl:42])=[CH:37][CH:36]=3)[CH:31]=2)[C:12]([NH2:15])=[N:13][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic Acid (2.500 mL) was added to a solution of tert-butyl N-[5-bromo-3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (500 mg, 0.8836 mmol) in dichloromethane (20.00 mL) and the mixture was stirred at ambient temperature for 10 minutes. The reaction mixture was concentrated in vacuo to give 5-bromo-3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]pyrazin-2-amine (323.1 mg, assumed 100% yield) which was used as such in next step. LC/MS m/z 365.4 [M−H]− Step 2: 5-bromo-3-[3-[4-(chloromethyl)phenyl]isoxazol-5-yl]pyrazin-2-amine was dissolved in ethanol, methanamine in ethanol (2.495 g, 3.300 mL, 26.51 mmol) was added and the mixture was stirred at 70° C. in a microwave. The reaction mixture was concentrated in vacuo. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. Combined organic extract was dried (MgSO4) and concentrated in vacuo yielding 5-bromo-3-(3-(4-((methylamino)methyl)phenyl)isoxazol-5-yl)pyrazin-2-amine as an oil that was used without further purification.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
Sources & evidence
- ORD record
- ord-113d9d6db0c544338312426a5e21437c
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877759B2
Reaction notes
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