Methyl 5-chloropyrazine-2-carboxylate → 5-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyrazine-2-carboxylic acid methyl ester
Reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][NH2:14].[CH3:15][O:16][C:17]([C:19]1[CH:24]=[N:23][C:22](Cl)=[CH:21][N:20]=1)=[O:18]>CS(C)=O>[CH3:15][O:16][C:17]([C:19]1[CH:24]=[N:23][C:22]([NH:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:21][N:20]=1)=[O:18]Participants
4
Procedure
A solution of (5-methyl-3-phenyl-4-isoxazolyl)methylamine (2.4 g, 12.7 mmol) and 5-chloro-pyrazine-2-carboxylic acid methyl ester (2.2 g, 12.7 mmol) in DMSO (15 mL) was heated with microwave irradiation to 160° C. for 30 min. After cooling to room temperature the reaction mixture was extracted with ethyl acetate, and the combined extracts were washed with water. The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 20:80). The oily product obtained was triturated with diisopropylether and ethyl acetate to afford the title compound (3.5 g, 84%) as an off-white solid. MS: m/e=325.4[M+H]+.
Workup
- extractionwas extracted with ethyl acetate
- washthe combined extracts were washed with water
- dry with materialThe organic phase was dried over sodium sulfate
- concentrationconcentrated
- customchromatographed (SiO2, heptane:ethyl acetate=100:0 to 20:80)
- customThe oily product obtained
- customwas triturated with diisopropylether and ethyl acetate
Sources & evidence
- ORD record
- ord-bc7b10695aa54050a76b60b340088ad2
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07902201B2
Reaction notes
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