Methanol → HCID 178424773, compound

HRID 43102Notes

Reaction equation

HRID 43102 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:10]=[C:11]([N+:14]([O-])=O)[NH:12][CH:13]=2)[CH2:4][CH2:3]1.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[C:25]1[C:34]2[N:33]=[CH:32][CH:31]=[N:30][C:29]=2[C:28]([C:35](O)=[O:36])=[CH:27][CH:26]=1.CO.C1COCC1.CO>[Ni].C(Cl)Cl.CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:10]=[C:11]([NH:14][C:35]([C:28]3[C:29]4[N:30]=[CH:31][CH:32]=[N:33][C:34]=4[C:25]([C:19]4[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=4[CH3:17])=[CH:26][CH:27]=3)=[O:36])[NH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 669145748-(2,6-Dimethyl-phenyl)quinoxaline-5-carboxylic acidHCID 178480844HCID 178480844, compound

Product 1

HCID 178424773HCID 178424773, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared in analogy to the procedures described in Example 14 but stirring the reaction mixture for at 60° C. overnight, using 1-methyl-4-(2-nitro-1H-imidazol-4-ylmethyl)-piperazine (Step 20.1) instead of 2-nitroimidazole in Step 14.3 and 8-(2,6-dimethylphenyl)-quinoxaline-5-carboxylic acid (Example 71), and using Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2. Title compound: ESI-MS: 456.1 [M+H]+; tR=3.18 min (System 1); TLC: Rf=0.15 (DCM/MeOH, 9:1).

Workup

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

Sources & evidence

ORD record
ord-e248b287c12545c5bcfaf8d7e0484aaa
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

Loading…