Pyridine → N-(2-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiazol-5-yl)-N'-(thiazol-2-yl)urea

HRID 387848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387848
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([NH2:21])=[CH:19][N:20]=1.N1C=CC=CC=1.Cl[C:29](OC1C=CC([N+]([O-])=O)=CC=1)=[O:30].[NH2:41][C:42]1[S:43][CH:44]=[CH:45][N:46]=1>O1CCCC1.CO.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[S:17][C:18]([NH:21][C:29]([NH:41][C:42]2[S:43][CH:44]=[CH:45][N:46]=2)=[O:30])=[CH:19][N:20]=1

Komponenten

10

Edukt 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 821294-Nitrophenyl chloroformateHCID 229363012-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiazol-5-ylamine

Produkt 1

HCID 22936997N-(2-(6,7-Dimethoxyquinolin-4-ylsulfanyl)thiazol-5-yl)-N'-(thiazol-2-yl)ureaAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

After dissolving 2-(6,7-dimethoxyquinolin-4-ylsulfanyl)thiazol-5-ylamine (216 mg, 0.676 mmol) and pyridine (58.8 mg, 0.743 mmol) in tetrahydrofuran (3 ml), 4-nitrophenyl chloroformate (150 mg, 0.743 mmol) was added while cooling on ice, the mixture was stirred at room temperature for 30 minutes, 2-aminothiazole (101 mg, 1.01 mmol) and triethylamine (1 ml) were added, and the mixture was heated and stirred at 60° C. for 1 hour. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline 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=30:1), 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 (57 mg, 0.128 mmol, 19%) as colorless crystals.

Aufarbeitung

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. temperaturethe mixture was heated
  4. stirringstirred at 60° C. for 1 hour
  5. washthe organic layer was washed with water and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationthe drying agent was filtered off
  8. distillationthe filtrate was distilled off under reduced pressure
  9. customThe obtained crude product
  10. additionthe fraction containing the target substance
  11. concentrationwas concentrated
  12. additiondiluted with hexane
  13. filtrationafter which the crystals were filtered out
  14. washwashed with hexane
  15. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-13d776d2730e4f98ae9216c1f9a33e46
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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