Tetrahydrofuran → HCID 178462567, Verbindung

HRID 641013

Reaktionsgleichung

CN1CCN(C2C=CC(N[CH:15]=[C:16]3[C:24]4[C:19](=[CH:20][C:21]([C:25]([C:27]5[CH:28]=[C:29]([NH:33][C:34]([C:36]6[C:40]([Cl:41])=[CH:39][N:38]([CH2:42][CH3:43])[N:37]=6)=[O:35])[CH:30]=[CH:31][CH:32]=5)=[O:26])=[CH:22][CH:23]=4)[NH:18][C:17]3=[O:44])=CC=2)CC1.C1COCC1.[N:50]1([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([NH2:62])=[CH:58][CH:57]=2)[CH2:54][CH2:53][CH2:52][CH2:51]1>CCOC(C)=O.CCCCCC>[O:44]=[C:17]1[C:16](=[CH:15][NH:62][C:59]2[CH:58]=[CH:57][C:56]([CH2:55][N:50]3[CH2:54][CH2:53][CH2:52][CH2:51]3)=[CH:61][CH:60]=2)[C:24]2[C:19](=[CH:20][C:21]([C:25]([C:27]3[CH:28]=[C:29]([NH:33][C:34]([C:36]4[C:40]([Cl:41])=[CH:39][N:38]([CH2:42][CH3:43])[N:37]=4)=[O:35])[CH:30]=[CH:31][CH:32]=3)=[O:26])=[CH:22][CH:23]=2)[NH:18]1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A small screw cap test tube was charged with 4-Chloro-1-ethyl-1H-pyrazole-3-carboxylic acid [3-(3-{[4-(4-methyl-piperazin-1-yl)-phenylamino]-methylene}-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 342, 100 mg, 0.229 mmol) and THF (2.5 mL). To the resulting solution was added 4-Pyrrolidin-1-ylmethyl-phenylamine (40.3 mg, 0.229 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 (˜40 mL). The solid that precipitated was collected by filtration and washed with 0° C. acetone (˜10 mL) affording the title compound in 31% yield (0.043 g, 0.072 mmol).

Aufarbeitung

customA small screw cap test tube
temperatureSubsequently, the reaction mixture was cooled to room temperature
customThe solid that precipitated
filtrationwas collected by filtration
washwashed with 0° C. acetone (˜10 mL)

Quellen und Nachweise

ORD-Eintrag: ord-0e1a3aac72fe428889a9fc139efcfd88
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07692005B2

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