O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 8-Naphthalen-1-yl-quinoxaline-5-carboxylic acid [5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide
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:16]([C:18]3[C:19]4[N:20]=[CH:21][CH:22]=[N:23][C:24]=4[C:25]([C:28]4[C:33](Cl)=[C:32](OC)[CH:31]=[C:30](OC)[C:29]=4Cl)=[CH:26][CH:27]=3)=[O:17])=[N:13][CH:14]=2)[CH2:4][CH2:3]1.CN(C(ON1N=N[C:50]2[CH:51]=CC=[CH:54][C:49]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCN(C2C=CC(NC(C3C4N=CC=NC=4C(C4C5C(=CC=CC=5)C=CC=4)=CC=3)=O)=CC=2)CC1>C(Cl)Cl.CO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]3[C:19]4[N:20]=[CH:21][CH:22]=[N:23][C:24]=4[C:25]([C:28]4[C:33]5[C:32](=[CH:54][CH:49]=[CH:50][CH:51]=5)[CH:31]=[CH:30][CH:29]=4)=[CH:26][CH:27]=3)=[O:17])=[N:13][CH:14]=2)[CH2:6][CH2:7]1Participants
5
Reactant 3
HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate
HCID 445147468-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-yl]-amide
HCID 445153558-Naphthalen-1-yl-quinoxaline-5-carboxylic acid [4-(4-methyl-piperazin-1-yl)phenyl]-amideProduct 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared in analogy to the procedure described in Step 14.1 but stirring the reaction mixture for 72 h at rt and using 3 equiv of 5-(4-methyl-piperazin-1-ylmethyl)-pyridin-2-ylamine hydrochloride (Example 31), TBTU (2.4 equiv) and 8-naphthalen-1-yl-quinoxaline-5-carboxylic acid (Example 46). Title compound: ESI-MS: 489.1 [M+H]+; tR=3.73 min (System 1); TLC: Rf=0.08 (DCM/MeOH, 9:1).
Workup
- customThe title compound was prepared in analogy to the procedure
Sources & evidence
- ORD record
- ord-5a1dd637fbe847ac95b9bf83725bd000
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273882B2
Reaction notes
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