N-(3-Aminopropyl)morpholine → 4-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]-N-(3-morpholin-4-ylpropyl)benzamide

HRID 884650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884650
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:27][CH2:26]1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCC[N+](C)(C)C.[I-]>ClC(Cl)C.CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:34][CH2:33][CH2:32][CH2:31][N:28]4[CH2:29][CH2:30][O:25][CH2:26][CH2:27]4)=[O:21])=[CH:17][CH:16]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:24]

Komponenten

7

Edukt 4

HCID 61055N-(3-Aminopropyl)morpholineHCID 757711-HydroxybenzotriazoleHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 1359001814-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid2×

Produkt 1

HCID 1359001824-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]-N-(3-morpholin-4-ylpropyl)benzamideAusbeute 27,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

4-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid (Compound 265, 15.5 mg, 48 umol) and 3-morpholinopropan-1-amine (5.8 mg, 40 umol) were dissolved in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL). To this solution was added 1-hydroxybenzotriazole (6.8 mg, 50 umol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (17.8 mg, 60 umol). The reaction mixture was stirred at room temperature for 15 hours and was concentrated in vacuo. The reaction mixture was purified by reverse phase HPLC to give 5 mg of product. 1H-NMR (400 MHz, d6-DMSO): δ 8.64-8.69 (m, 1H), 8.19-8.27 (m, 3H), 7.94-8.01 (m, 3H), 7.86-7.91 (d, 1H), 7.50 (s, 1H), 6.88-6.95 (d, 1H), 3.54-3.60 (m, 4H), 3.27-3.36 (m, 4H), 2.29-2.41 (m, 4H), 2.21 (s, 3H), 1.65-1.77 (m, 2H). MS (EI): 449.5 (MH+).

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. customThe reaction mixture was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a83a3ab1084f441685f877caffa17119
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242129B2

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