Tetrahydrofuran → 3-[4-[[6-[3-[(5-chloro-1-methylpyrazole-4-carbonyl)amino]benzoyl]-2-oxo-1H-indol-3-ylidene]methylamino]phenyl]propanoic acid

HRID 641039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 641039
O[CH:2]=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[CH:15]=[C:16]([NH:20][C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:29])[C:27]=4[Cl:28])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:30].C1COCC1.[NH2:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[CH:39][CH:38]=1>CCOC(C)=O.CCCCCC>[Cl:28][C:27]1[N:26]([CH3:29])[N:25]=[CH:24][C:23]=1[C:21]([NH:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:3](=[CH:2][NH:36][C:37]3[CH:38]=[CH:39][C:40]([CH2:43][CH2:44][C:45]([OH:47])=[O:46])=[CH:41][CH:42]=3)[C:4](=[O:30])[NH:5]2)=[CH:10][CH:9]=1)=[O:13])=[O:22]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 754513-(4-Aminophenyl)propionic acidHCID 178481853HCID 178481853, Verbindung

Produkt 1

HCID 1784818513-[4-[[6-[3-[(5-chloro-1-methylpyrazole-4-carbonyl)amino]benzoyl]-2-oxo-1H-indol-3-ylidene]methylamino]phenyl]propanoic acidAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A small screw cap test tube was charged with 5-Chloro-1-methyl-1H-pyrazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 328, 100 mg, 0.2365 mmol) and THF (2.5 mL). To the resulting solution was added 3-(4-Amino-phenyl)-propionic acid (39.1 mg, 0.237 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and diluted with EtOAc (˜5 mL) and Hexane (˜50 mL). The precipitate that formed was collected by filtration and washed with acetone (˜15 mL) to afford the title compound in 57% yield (0.077 g, 0.1351 mmol).

Aufarbeitung

  1. customA small screw cap test tube
  2. temperatureSubsequently, the reaction mixture was cooled to room temperature
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with acetone (˜15 mL)

Quellen und Nachweise

ORD-Eintrag
ord-8b614bec18e24c17840ee3d4e2821053
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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