Methanol → HCID 178493491, compound

HRID 43126Notes

Reaction equation

HRID 43126 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]1[C:21]2[N:20]=[CH:19][CH:18]=[N:17][C:16]=2[C:15]([C:22]([OH:24])=O)=[CH:14][CH:13]=1.[N+:25]([C:28]1[NH:29][CH:30]=[C:31]([CH2:33][N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[N:32]=1)([O-])=O.CO.C1COCC1.CO>[Ni].C(Cl)Cl.CO>[N:34]1([CH2:33][C:31]2[N:32]=[C:28]([NH:25][C:22]([C:15]3[C:16]4[N:17]=[CH:18][CH:19]=[N:20][C:21]=4[C:12]([C:3]4[CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=4[F:1])=[CH:13][CH:14]=3)=[O:24])[NH:29][CH:30]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 592928668-(2-Fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acidHCID 1785268981H-Imidazole, 2-nitro-4-(1-pyrrolidinylmethyl)-

Product 1

HCID 178493491HCID 178493491, 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-fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid (Step 94.1). 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: 477.2 [M+H]+; tR=3.28 min (System 1); TLC: Rf=0.11 (DCM/MeOH/NH3aq, 94:5:1).

Workup

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

Sources & evidence

ORD record
ord-9f1ef75023b74d35933ae4fdbcf9fda2
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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