Diisopropylethylamine → N-(2,6-Diethylphenyl)-1-methyl-8-({1-[(4-methylpiperazin-1-yl)carbonyl]piperidin-4-yl}amino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81958

Reaktionsgleichung

Reaktionsgleichung von HRID 81958
Cl.[CH2:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:5]=1[NH:12][C:13]([C:15]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:25]([NH:28][CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[N:26][C:27]=3[C:18]=2[N:17]([CH3:35])[N:16]=1)=[O:14])[CH3:3].CCN(C(C)C)C(C)C.[CH3:45][N:46]1[CH2:51][CH2:50][N:49]([C:52](Cl)=[O:53])[CH2:48][CH2:47]1>ClCCl.ClCCl.CO>[CH2:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:2][CH3:3])[C:5]=1[NH:12][C:13]([C:15]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:25]([NH:28][CH:29]4[CH2:30][CH2:31][N:32]([C:52]([N:49]5[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]5)=[O:53])[CH2:33][CH2:34]4)=[N:26][C:27]=3[C:18]=2[N:17]([CH3:35])[N:16]=1)=[O:14])[CH3:11]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 44555920N-(2,6-diethylphenyl)-1-methyl-8-(piperidin-4-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide hydrochloride

Produkt 1

HCID 44555971N-(2,6-Diethylphenyl)-1-methyl-8-({1-[(4-methylpiperazin-1-yl)carbonyl]piperidin-4-yl}amino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of N-(2,6-diethylphenyl)-1-methyl-8-(piperidin-4-ylamino)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide hydrochloride (40 mg, 0.075 mmol) in dichloromethane (1 mL) at 0° C., DIPEA (0.2 mL, 1.1 mmol), and 4-methylpiperazine-1-carbonyl chloride (17 mg, 0.09 mmol) were added. The mixture was then stirred at room temperature for 3 h. Solvent evaporated to dryness and the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol: 9/1) to 38 mg of the title compound (86% yield).

Aufarbeitung

  1. customSolvent evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-44292c195270465d88a2b01f989626b9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846701B2

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