Formic Acid → HCID 86613583, compound

HRID 1983193Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:26])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1.[CH:27](O)=[O:28]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:26][CH:27]=[O:28])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1

Participants

Reactant 2

HCID 284Formic Acid

HCID 167225873-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

Product 1

HCID 86613583HCID 86613583, compoundYield 10%

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]-oxadiazol-2-yl]-phenylamine (200 mg, 0.57 mmol) and formic acid (2.1 mL, 55.6 mmol) was stirred at 90° C. for 2 h. After concentration purification of the residue by chromatography (SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:95:5) afforded the title compound (21 mg, 10%) as a yellow solid. MS: m/e=377.3 [M+H]+.

Workup

concentrationAfter concentration purification of the residue by chromatography (SiO2, heptane:ethyl acetate:methanol=50:50:0 to 0:95:5)

Sources & evidence

ORD record: ord-62ed7476590941379e5a7dcd02dde049
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541372B2

Reaction notes

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