Methanol → HCID 178493496, compound

HRID 2391923Notes

Reaction equation

HRID 2391923 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[N:8]=CC=N[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.[CH3:28][N:29]([CH3:39])[CH2:30][C:31]1[N:32]=[C:33]([N+:36]([O-])=O)[NH:34][CH:35]=1.CO.[CH2:42]1[CH2:46]OC[CH2:43]1.CO>[Ni].C(Cl)Cl.CO>[CH3:28][N:29]([CH2:30][C:31]1[N:32]=[C:33]([NH:36][C:4]([C:6]2[CH:15]=[CH:14][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])=[C:12]3[C:7]=2[N:8]=[CH:46][CH:42]=[CH:43]3)=[O:3])[NH:34][CH:35]=1)[CH3:39]

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 178493496HCID 178493496, 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), stirring the reaction mixture for 7 h at 70° C., and using dimethyl-(2-nitro-1H-imidazol-4-ylmethyl)-amine (Step 22.1) instead of 2-nitroimidazole in Step 14.3, and Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2. The title compound: ESI-MS: 468.1 [M+H]+; tR=3.29 min (System 1); TLC: Rf=0.18 (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-60718f6764ba42f9847b47a4424fb932
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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