Methanol → HCID 178493457, compound

HRID 43187Notes

Reaction equation

HRID 43187 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[Cl:27])=[CH:14][CH:15]=1)=O)C.CO.C1COCC1.CO.[CH3:37][N:38]1[CH2:43][CH2:42][N:41]([CH2:44][C:45]2[N:46]=[C:47]([N+:50]([O-])=O)[NH:48][CH:49]=2)[CH2:40][CH2:39]1>[Ni].C(Cl)Cl.CO>[CH3:37][N:38]1[CH2:43][CH2:42][N:41]([CH2:44][C:45]2[N:46]=[C:47]([NH:50][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:3])[NH:48][CH:49]=2)[CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 866411468-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid ethyl esterHCID 178480844HCID 178480844, compound

Product 1

HCID 178493457HCID 178493457, 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 1-methyl-4-(2-nitro-1H-imidazol-4-ylmethyl)-piperazine (Step 20.1) instead of 2-nitroimidazole in Step 14.3. Title compound: ESI-MS: 540.0 [M+H]+; tR=3.07 min (System 1); TLC: Rf=0.23 (DCM/MeOH/NH3aq, 94:5:1).

Workup

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

Sources & evidence

ORD record
ord-2d16b2cb220748c08f429267a668ad39
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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