Methanol → HCID 178493495, compound

HRID 43168Notes

Reaction equation

HRID 43168 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.[N+:28]([C:31]1[NH:32][CH:33]=[C:34]([CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[N:35]=1)([O-])=O.CO.C1COCC1.CO>[Ni].C(Cl)Cl.CO>[N:37]1([CH2:36][C:34]2[N:35]=[C:31]([NH:28][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:17]([F:27])=[C:18]([O:25][CH3:26])[CH:19]=[C:20]([O:23][CH3:24])[C:21]=4[F:22])=[CH:14][CH:15]=3)=[O:5])[NH:32][CH:33]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 866411458-(2,6-Difluoro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid ethyl esterHCID 178526899HCID 178526899, compound

Product 1

HCID 178493495HCID 178493495, 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 stirring the reaction mixture for 2 h at 70° C. and using 8-(2,6-difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid ethyl ester (Step 124.1). 4-(2-Nitro-1H-imidazol-4-ylmethyl)morpholine (Step 23.1) was used 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: 511.1 [M+H]+; tR=3.21 min (System 1); TLC: Rf=0.34 (DCM/MeOH/NH3aq, 94:5:1).

Workup

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

Sources & evidence

ORD record
ord-825d677469ea409fa57e34010829afb5
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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