Tetrahydrofuran → 5-chloro-1-methyl-N-[3-[2-oxo-3-[[4-(2-pyrrolidin-1-ylethyl)anilino]methylidene]-1H-indole-6-carbonyl]phenyl]pyrazole-4-carboxamide

HRID 2352972

Reaktionsgleichung

Reaktionsgleichung von HRID 2352972
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.[N:36]1([CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1>CCOC(C)=O.CCCCCC>[O:30]=[C:4]1[C:3](=[CH:2][NH:49][C:46]2[CH:47]=[CH:48][C:43]([CH2:42][CH2:41][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[CH:44][CH:45]=2)[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]1

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 64870474-(2-(Pyrrolidin-1-yl)ethyl)anilineHCID 178481853HCID 178481853, Verbindung

Produkt 1

HCID 1784818525-chloro-1-methyl-N-[3-[2-oxo-3-[[4-(2-pyrrolidin-1-ylethyl)anilino]methylidene]-1H-indole-6-carbonyl]phenyl]pyrazole-4-carboxamideAusbeute 29 %

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 4-(2-Pyrrolidin-1-yl-ethyl)-phenylamine (45 mg, 0.236 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 29% yield (0.041 g, 0.0689 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-b5feee2ff909495a91624f64e6ea3699
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749530B2

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