Methanol → HCID 178493492, compound

HRID 43121Notes

Reaction equation

HRID 43121 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[C:22]2[N:21]=[CH:20][CH:19]=[N:18][C:17]=2[C:16]([C:23](O)=[O:24])=[CH:15][CH:14]=1.[N+:26]([C:29]1[NH:30][CH:31]=[C:32]([CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[N:33]=1)([O-])=O.CO.C1COCC1.CO>[Ni].C(Cl)Cl.CO>[N:35]1([CH2:34][C:32]2[N:33]=[C:29]([NH:26][C:23]([C:16]3[C:17]4[N:18]=[CH:19][CH:20]=[N:21][C:22]=4[C:13]([C:3]4[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=4[F:12])=[CH:14][CH:15]=3)=[O:24])[NH:30][CH:31]=2)[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 592928348-(2,6-Difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acidHCID 1785268981H-Imidazole, 2-nitro-4-(1-pyrrolidinylmethyl)-

Product 1

HCID 178493492HCID 178493492, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
65 °C

Procedure

The title compound was prepared in analogy to the procedures described in Example 14 but stirring the reaction mixture for 6 h at 65° C. and using 8-(2,6-difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid (Step 88.1). 2-Nitro-4-pyrrolidin-1-ylmethyl-1H-imidazole (Step 19.1) instead of 2-nitroimidazole was used 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: 495.0 [M+H]+; tR=3.28 min (System 1); TLC: Rf=0.08 (DCM/MeOH/NH3aq, 94:5:1).

Workup

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

Sources & evidence

ORD record
ord-82bfa70907c248358de3024fba870bcd
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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