Methyl chloroglyoxylate → n-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-oxalamic 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][O:14][C:15]1[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.[CH3:22][O:23][C:24]([C:26](Cl)=[O:27])=[O:25]>>[CH3:22][O:23][C:24](=[O:25])[C:26]([NH:21][C:18]1[CH:19]=[N:20][C:15]([O: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:16][CH:17]=1)=[O:27]Participants
3
Procedure
As described for example 179b, 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-ylamine (150 mg, 0.53 mmol) was converted, using methyloxalylchloride instead of acetyl chloride, to the title compound (118 mg, 60%) which was obtained as a white solid after purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 9:1). MS: m/e=368.0 [M+H]+.
Sources & evidence
- ORD record
- ord-02f9b15228d045e381140a5c80f4da6b
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877782B2
Reaction notes
Loading…