HCID 53248667, compound → HCID 53248668, compound

HRID 2357935Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=[C:7]2[C:6]([C:15]2[CH:16]=[CH:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:5][CH:4]=1>[Zn].C(O)(=O)C>[CH3:1][O:2][C:3]1[N:8]2[N:9]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=[C:7]2[C:6]([C:15]2[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the compound of Example 276 (45 mg), zinc (52 mg) and acetic acid (1.6 mL) was stirred at 100° C. for 30 min. The insoluble material was removed by filtration and the filtrate was concentrated. A saturated sodium bicarbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with 0.1 mol/LEDTA disodium solution and saturated brine and dried over magnesium sulfate. The solvent was concentrated and the resulting residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:9) to afford the title compound as a pale yellow oil (16 mg).

Workup

customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated
additionA saturated sodium bicarbonate solution was added to the residue
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed sequentially with 0.1 mol/LEDTA disodium solution and saturated brine
dry with materialdried over magnesium sulfate
concentrationThe solvent was concentrated
customthe resulting residue was purified by silica gel column chromatography (methanol:ethyl acetate=1:9)

Sources & evidence

ORD record: ord-4c99474375784596aa5879501fc13a58
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763617B2

Reaction notes

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