O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 8-(4-Methyl-thiophen-3-yl)-quinoxaline-5-carboxylic acid [5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide

HRID 43095

Reaction equation

HRID 43095 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15]C(C3C4N=CC=NC=4C(C4C(Cl)=C(OC)C=C(OC)C=4Cl)=CC=3)=O)=[N:13][CH:14]=2)[CH2:4][CH2:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:62][C:63]1[C:64]([C:68]2[C:77]3[N:76]=[CH:75][CH:74]=[N:73][C:72]=3[C:71]([C:78]([OH:80])=O)=[CH:70][CH:69]=2)=[CH:65][S:66][CH:67]=1.CC1C(B(O)O)=CSC=1>C(Cl)Cl.CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:78]([C:71]3[C:72]4[N:73]=[CH:74][CH:75]=[N:76][C:77]=4[C:68]([C:64]4[C:63]([CH3:62])=[CH:67][S:66][CH:65]=4)=[CH:69][CH:70]=3)=[O:80])=[N:13][CH:14]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 50839314-Methyl-3-thiopheneboronic acidHCID 445147468-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amideHCID 669145508-(4-Methylthiophen-3-yl)-quinoxaline-5-carboxylic acid

Product 1

HCID 445162828-(4-Methyl-thiophen-3-yl)-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 at it overnight, using 2 equiv of 5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochloride (Example 31), TBTU (2 equiv) and 8-(4-methylthiophen-3-yl)-quinoxaline-5-carboxylic acid. The carboxylic acid was synthesized as described in Steps 1.2-1.7 but using 4-methyl-3-thiopheneboronic acid in Step 1.4. Title compound: ESI-MS: 459.1 [M+H]+; tR=3.41 min (System 1); TLC: Rf=0.25 (DCM/MeOH, 9:1).

Workup

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

Sources & evidence

ORD record
ord-c21067481caf4224b7963a2d270b5f6a
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Linked notes

Loading…