[(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate → 2-Chloro-N-{2-oxo-1-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl]-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247510Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247510
[NH2:1]/[C:2](=[N:27]\[O:28][C:29](OCC)=[O:30])/[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]([NH:14][C:15]([C:17]2[NH:21][C:20]3[S:22][C:23]([Cl:25])=[CH:24][C:19]=3[CH:18]=2)=[O:16])[C:5]1=[O:26]>O1CCOCC1>[Cl:25][C:23]1[S:22][C:20]2[NH:21][C:17]([C:15]([NH:14][CH:6]3[CH2:7][C:8]4[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=4)[N:4]([CH2:3][C:2]4[NH:1][C:29](=[O:30])[O:28][N:27]=4)[C:5]3=[O:26])=[O:16])=[CH:18][C:19]=2[CH:24]=1

Komponenten

3

Edukt 1

HCID 21906825[(Z)-[1-amino-2-[3-[(2-chloro-6H-thieno[2,3-b]pyrrole-5-carbonyl)amino]-2-oxo-3,4-dihydroquinolin-1-yl]ethylidene]amino] ethyl carbonate

Produkt 1

HCID 1354575442-Chloro-N-{2-oxo-1-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)methyl]-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-[1-((2Z)-2-Amino-2-{[(ethoxycarbonyl)oxy]imino}ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 14) was dissolved in 1,4-Dioxane and the solvent distilled off with the oil bath temperature 140° C. This was repeated 4 times. The residual solid was triturated with refluxing Et2O (10 mL) and after cooling filtered, washed with Et2O (10 mL) and hexane (10 mL) to give the title product (184 mg, 87% (2 steps)) as a pale brown solid.

Aufarbeitung

  1. distillationthe solvent distilled off with the oil bath temperature 140° C
  2. customThe residual solid was triturated with refluxing Et2O (10 mL)
  3. temperatureafter cooling
  4. filtrationfiltered
  5. washwashed with Et2O (10 mL) and hexane (10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-0b82fd1174eb448bbf46a6843e94457a
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129249B2

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