Methanol → HCID 178493497, compound

HRID 43163Notes

Reaction equation

HRID 43163 reaction equation
C(O[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:5])C.CO.C1COCC1.CO.[CH3:37][N:38]([CH3:48])[CH2:39][C:40]1[N:41]=[C:42]([N+:45]([O-])=O)[NH:43][CH:44]=1>[Ni].C(Cl)Cl.CO>[CH3:37][N:38]([CH2:39][C:40]1[N:41]=[C:42]([NH:45][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:17]([F:27])=[C:18]([O:25][CH3:26])[CH:19]=[C:20]([O:23][CH3:24])[C:21]=3[F:22])=[CH:14][CH:15]=2)=[O:5])[NH:43][CH:44]=1)[CH3:48]

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 866411458-(2,6-Difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid ethyl esterHCID 178483302HCID 178483302, compound

Product 1

HCID 178493497HCID 178493497, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

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), Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2, dimethyl-(2-nitro-1H-imidazol-4-ylmethyl)-amine (Step 22.1) instead of 2-nitroimidazole in Step 14.3. The title compound: ESI-MS: 469.1 [M+H]+; tR=3.15 min (System 1); TLC: Rf=0.22 (DCM/MeOH/NH3aq, 91.5:7.5:1).

Workup

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

Sources & evidence

ORD record
ord-588419b3129343919816e53c9554aeda
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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