Methanol → HCID 178431882, compound

HRID 43097

Reaction equation

HRID 43097 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.CO.C1COCC1.CO.[CH3:26][C:27]1[C:28]([C:32]2[C:41]3[N:40]=[CH:39][CH:38]=[N:37][C:36]=3[C:35]([C:42](O)=[O:43])=[CH:34][CH:33]=2)=[CH:29][S:30][CH:31]=1>[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:42]([C:35]3[C:36]4[N:37]=[CH:38][CH:39]=[N:40][C:41]=4[C:32]([C:28]4[C:27]([CH3:26])=[CH:31][S:30][CH:29]=4)=[CH:33][CH:34]=3)=[O:43])[NH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 669145508-(4-Methylthiophen-3-yl)-quinoxaline-5-carboxylic acidHCID 178480844HCID 178480844, compound

Product 1

HCID 178431882HCID 178431882, 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 16 h at 60° C., using 1-methyl-4-(2-nitro-1H-imidazol-4-ylmethyl)-piperazine (Step 20.1) instead of 2-nitroimidazole in Step 14.3, Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2, and 8-(4-methylthiophen-3-yl)-quinoxaline-5-carboxylic acid (Example 67) in Step 14.1. Title compound: ESI-MS: 448.0 [M+H]+; tR=3.00 min (System 1); TLC: Rf=0.14 (DCM/MeOH, 9:1).

Workup

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

Sources & evidence

ORD record
ord-3421b637912e46d1aeccae0efc2b9fbd
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

Loading…