Water → 7-Methoxy-4-(5-(3-thiazol-2-ylureido)thiophen-2-ylsulfanyl)quinoline-6-carboxamide

HRID 1010239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010239
[NH2:1][C:2]1[S:6][C:5]([S:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH3:22])=[C:15]([C:18]([NH2:20])=[O:19])[CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1([O:29][C:30](=O)[NH:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)C=CC=CC=1.C(OCC)(=O)C.O>CS(C)=O.CO>[CH3:22][O:21][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([S:7][C:5]3[S:6][C:2]([NH:1][C:30]([NH:31][C:32]4[S:33][CH:34]=[CH:35][N:36]=4)=[O:29])=[CH:3][CH:4]=3)=[CH:9][CH:10]=[N:11]2)=[CH:16][C:15]=1[C:18]([NH2:20])=[O:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateHCID 229362694-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide

Produkt 1

HCID 229368697-Methoxy-4-(5-(3-thiazol-2-ylureido)thiophen-2-ylsulfanyl)quinoline-6-carboxamideAusbeute 38,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

4-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide (66.0 mg, 0.200 mmol) and thiazol-2-ylcarbamic acid phenyl ester (66.0 mg, 0.300 mmol) were stirred in dimethylsulfoxide (1 ml) at 85° C. for 2 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate:methanol=15:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (35.0 mg, 0.077 mmol, 38%) as colorless crystals.

Aufarbeitung

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additiondiluted with hexane
  9. filtrationafter which the crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-d3376517ba0741cbafa63913fcf37e4b
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973160B2

Notizen zur Reaktion

Wird geladen…