Methanol → HCID 70665058, compound

HRID 1403396Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([C:10]2[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=4)=[O:26])[CH:16]=3)[N:11]=2)[CH:6]=[CH:7][C:8]=1[OH:9])=O.[NH2:37]OS(O)(=O)=O.CO>O>[O:9]1[C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25]([O:27][CH2:28][C:29]5[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=5)=[O:26])[CH:16]=4)[N:11]=3)=[CH:4][C:3]=2[CH:1]=[N:37]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (4-methoxyphenyl)methyl 2-(3-formyl-4-hydroxyphenyl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (190 mg, 0.39 mmol) in water (5 mL) was added aminooxysulfonic acid (83 mg, 0.48 mmol) and methanol (5 mL). The resulting solution was stirred overnight at 25° C. Then the reaction was quenched by the addition of water (200 mL) and extracted with ethyl acetate (3×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography eluting with 1% to 5% ethyl acetate in petroleum to afford (4-methoxyphenyl)methyl 2-(1,2-benzoxazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate as a yellow solid (50 mg, 26%).

Workup

customThen the reaction was quenched by the addition of water (200 mL)
extractionextracted with ethyl acetate (3×50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by silica gel column chromatography
washeluting with 1% to 5% ethyl acetate in petroleum

Sources & evidence

ORD record: ord-4fea941b67754a1e9111f6dd758f6219
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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