Pyridine → 4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid methyl ester

HRID 2265182

Reaktionsgleichung

Reaktionsgleichung von HRID 2265182
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N:13]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([S:23](Cl)(=[O:25])=[O:24])[C:17]=2[N:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.C(Cl)Cl>CCOC(C)=O>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=1[NH:1][S:23]([C:18]1[C:17]2[N:16]=[CH:15][CH:14]=[N:13][C:22]=2[CH:21]=[CH:20][CH:19]=1)(=[O:24])=[O:25]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 80001Methyl 4-chloroanthranilateHCID 16090697Quinoxaline-5-sulfonyl chloride

Produkt 1

HCID 671992924-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid methyl esterAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 2-amino-4-chlorobenzoate (0.33 g, 1.8 mmol), quinoxaline-5-sulfonyl chloride (0.40 g, 1.8 mmol), pyridine (0.71 mL, 8.8 mmol), and DCM (10 mL) was stirred at rt for 16 h. EtOAc (75 mL) was added and the solution was washed with satd. aq. NaHCO3 (50 mL), then dried and concentrated. Chromatographic purification of this residue (EtOAc/hexanes) gave the title compound as a white solid (0.60 mg, 90%). MS (ESI+): mass calcd. for C16H12ClN3O4S, 377.0; m/z found, 378 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.44 (s, 1H), 8.97 (d, J=1.8, 1H), 8.95 (d, J=1.8, 1H), 8.61 (dd, J=7.4, 1.4, 1H), 8.33 (dd, J=8.5, 1.4, 1H), 7.89 (dd, J=8.4, 1.0, 1H), 7.84 (d, J=2.0, 1H), 7.77 (d, J=8.6, 1H), 6.89 (dd, J=8.6, 2.0, 1H), 3.90 (s, 3H).

Aufarbeitung

  1. washthe solution was washed with satd
  2. dry with materialaq. NaHCO3 (50 mL), then dried
  3. concentrationconcentrated
  4. customChromatographic purification of this residue (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-249a7dde4624468da5025f0d40e5365e
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855292B2

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