Methanol → HCID 178480841, compound

HRID 43081Notes

Reaction equation

HRID 43081 reaction equation
CN1CCN(C2C=CC(N[C:15]([C:17]3[C:18]4[N:19]=[CH:20][CH:21]=[N:22][C:23]=4[C:24]([C:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=[CH:29][CH:28]=4)=[CH:25][CH:26]=3)=[O:16])=CC=2)CC1.CO.C1COCC1.CO.[CH3:46][N:47]1[CH2:52][CH2:51][N:50]([CH2:53][C:54]2[N:55]=[C:56]([N+:59]([O-])=O)[NH:57][CH:58]=2)[CH2:49][CH2:48]1>[Ni].C(Cl)Cl.CO>[CH3:46][N:47]1[CH2:52][CH2:51][N:50]([CH2:53][C:54]2[N:55]=[C:56]([NH:59][C:15]([C:17]3[C:18]4[N:19]=[CH:20][CH:21]=[N:22][C:23]=4[C:24]([C:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=[CH:29][CH:28]=4)=[CH:25][CH:26]=3)=[O:16])[NH:57][CH:58]=2)[CH2:49][CH2:48]1

Participants

7

Reactant 4

HCID 887MethanolHCID 21899815MeOH tetrahydrofuranHCID 445153558-Naphthalen-1-yl-quinoxaline-5-carboxylic acid [4-(4-methyl-piperazin-1-yl)phenyl]-amideHCID 178480844HCID 178480844, compound

Product 1

HCID 178480841HCID 178480841, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedures described in Example 14 but using 8-naphthalen-1-yl-quinoxaline-5-carboxylic acid (Example 46) in Step 14.1, Raney nickel and MeOH/THF (1:1) instead of palladium on carbon and MeOH in Step 14.2 and 1-methyl-4-(2-nitro-1H-imidazol-4-ylmethyl)-piperazine (Step 20.1) instead of 2-nitroimidazole in Step 14.3. Title compound: ESI-MS: 478.1 [M+H]+; tR=3.36 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-2ca717b309df491c833649020f262490
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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