Methanol → HCID 178463869, compound

HRID 2391902Notes

Reaction equation

HRID 2391902 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[N:8]=[CH:9][CH:10]=[N:11][C:12]=2[C:13]([C:16]2[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=2[F:27])=[CH:14][CH:15]=1)=O)C.[CH2:28]([N:30]([CH3:40])[CH2:31][C:32]1[N:33]=[C:34]([N+:37]([O-])=O)[NH:35][CH:36]=1)[CH3:29].CO.C1COCC1.CO>[Ni].C(Cl)Cl.CO>[CH2:28]([N:30]([CH2:31][C:32]1[N:33]=[C:34]([NH:37][C:4]([C:6]2[C:7]3[N:8]=[CH:9][CH:10]=[N:11][C:12]=3[C:13]([C:16]3[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=3[F:27])=[CH:14][CH:15]=2)=[O:3])[NH:35][CH:36]=1)[CH3:40])[CH3:29]

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 866411458-(2,6-Difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid ethyl esterHCID 178463870HCID 178463870, compound

Product 1

HCID 178463869HCID 178463869, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
70 °C

Procedure

The title compound was prepared in analogy to the procedures described in Example 14 but using 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 124.1) and stirring the reaction mixture for 3 h at 70° C. Ethyl-methyl-(2-nitro-1H-imidazol-4-ylmethyl)-amine (Step 157.1) instead of 2-nitroimidazole was used in Step 14.3, and Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2. Title compound: ESI-MS: 483.9 [M+H]+; TLC: Rf=0.10 (DCM/MeOH, 9:1).

Workup

  1. customThe title compound was prepared in analogy to the procedures

Sources & evidence

ORD record
ord-ddc22844f251447db9639f489164d753
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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