O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 8-(2,6-Dimethyl-phenyl)-quinoxaline-5-carboxylic acid [5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

HRID 2409662Notes

Reaction equation

HRID 2409662 reaction equation
Cl.[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[N:14][CH:15]=2)[CH2:5][CH2:4]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[C:41]=1[C:47]1[C:56]2[N:55]=[CH:54][CH:53]=[N:52][C:51]=2[C:50]([C:57](O)=[O:58])=[CH:49][CH:48]=1>C(Cl)Cl.CO>[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:57]([C:50]3[C:51]4[N:52]=[CH:53][CH:54]=[N:55][C:56]=4[C:47]([C:41]4[C:42]([CH3:46])=[CH:43][CH:44]=[CH:45][C:40]=4[CH3:39])=[CH:48][CH:49]=3)=[O:58])=[N:14][CH:15]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669145625-(4-Methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochlorideHCID 669145748-(2,6-Dimethyl-phenyl)quinoxaline-5-carboxylic acid

Product 1

HCID 445166078-(2,6-Dimethyl-phenyl)-quinoxaline-5-carboxylic acid [5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but stirring the reaction mixture for 2 days at rt, using 2 equiv of 5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochloride (Example 31), TBTU (2 equiv) and 8-(2,6-dimethyl-phenyl)-quinoxaline-5-carboxylic acid (Example 71). Title compound: ESI-MS: 467.1 [M+H]+; tR=3.55 min (System 1); TLC: Rf=0.15 (DCM/MeOH, 9:1).

Workup

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

Sources & evidence

ORD record
ord-90a82ec4d2114ce18b6f2ad29efd28be
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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