Trimethyl orthoformate → HCID 69744208, compound

HRID 1760366Notes

Reaction equation

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

Participants

Reactant 2

HCID 9005Trimethyl orthoformate

HCID 69743184HCID 69743184, compound

Product 1

HCID 69744208HCID 69744208, compoundYield 97.4%

Procedure

A mixture of affording 1-[6-(4-Hydrazinocarbonyl-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.20 g, 0.44 mmol), trimethylorthoformate (0.1 mL, 0.91 mmol) and 1 mL of xylenes was refluxed for 24 hours. The mixture was concentrated in vacuo, affording 1-[6-(4-[1,3,4]oxadiazol-2-yl-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.2 g) as a colorless syrup. MS (APCl, m/z): 467.2 [M+H]+.

Workup

temperaturewas refluxed for 24 hours
concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-cdc8c005d3834e85b92778367ba222e7
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841671B2

Reaction notes

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