Methanol → HCID 178493458, compound

HRID 2391901Notes

Reaction equation

HRID 2391901 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[Cl:27])=[CH:14][CH:15]=1)=[O:5])C.CO.C1COCC1.CO.[N+:37]([C:40]1[NH:41][CH:42]=[C:43]([CH2:45][N:46]2[CH2:51][CH2:50][NH:49][C:48](=[O:52])[CH2:47]2)[N:44]=1)([O-])=O>[Ni].C(Cl)Cl.CO>[O:52]=[C:48]1[NH:49][CH2:50][CH2:51][N:46]([CH2:45][C:43]2[N:44]=[C:40]([NH:37][C:4]([C:6]3[C:7]4[N:8]=[CH:9][CH:10]=[N:11][C:12]=4[C:13]([C:16]4[C:21]([F:22])=[C:20]([O:23][CH3:24])[CH:19]=[C:18]([O:25][CH3:26])[C:17]=4[Cl:27])=[CH:14][CH:15]=3)=[O:5])[NH:41][CH:42]=2)[CH2:47]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 866411468-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl esterHCID 178516762HCID 178516762, compound

Product 1

HCID 178493458HCID 178493458, 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-chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl ester (Step 144.1), Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2, and 4-(2-nitro-1H-imidazol-4-ylmethyl)-piperazin-2-one (Step 142.1) instead of 2-nitroimidazole in Step 14.3. Title compound: ESI-MS: 540.0 [M+H]+; tR=3.18 min (System 1); TLC: Rf=0.18 (DCM/MeOH, 9:1).

Workup

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

Sources & evidence

ORD record
ord-24106f7d38f24d2982c43af363026abd
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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