Triethylamine → 8-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

HRID 43043

Reaktionsgleichung

Reaktionsgleichung von HRID 43043
CCCP(=O)=O.[Cl:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[C:10]([Cl:18])[C:9]=1[C:19]1[C:28]2[N:27]=[CH:26][CH:25]=[N:24][C:23]=2[C:22]([C:29]([OH:31])=O)=[CH:21][CH:20]=1.[CH2:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=2)[CH2:36][CH2:35]1)[CH3:33].CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O.O>[CH2:32]([N:34]1[CH2:35][CH2:36][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH:44][C:29]([C:22]3[C:23]4[N:24]=[CH:25][CH:26]=[N:27][C:28]=4[C:19]([C:9]4[C:8]([Cl:7])=[C:13]([O:14][CH3:15])[CH:12]=[C:11]([O:16][CH3:17])[C:10]=4[Cl:18])=[CH:20][CH:21]=3)=[O:31])=[CH:42][CH:41]=2)[CH2:38][CH2:39]1)[CH3:33]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 9367384-(4-Ethylpiperazin-1-yl)anilineHCID 16167369Propylphosphoric anhydrideHCID 592928388-(2,6-Dichloro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

Produkt 1

HCID 445135288-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of propylphosphonic anhydride (50% in DMF, 0.31 mL, 0.53 mmol, 2 equiv), 8-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (100 mg, 0.26 mmol) (Step 1.1), 4-(4-ethylpiperazin-1-yl)-aniline (Step 1.9) (65 mg, 0.32 mmol, 1.2 equiv), DMAP (2 mg), and Et3N (0.37 mL, 2.65 mmol, 10 equiv) in DMF (2.0 mL), was stirred for 18 h at rt, under an argon atmosphere. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc. The combined organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by trituration in Et2O to afford the title compound as a yellow solid: ES-MS: 565.9 [M+H]+; tR=4.26 min (System 1).

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by trituration in Et2O

Quellen und Nachweise

ORD-Eintrag
ord-28d5a761e9ea4cb595861a2c4423f7ec
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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