Diethylethanolamine → N-cyclopropyl-3-({4-[(6-{[2-(diethylamino)ethoxy]methyl}pyridin-2-yl)methoxy]benzoyl}amino)-4-methylbenzamide

HRID 550075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 550075
[H-].[Na+].[CH2:3]([N:5]([CH2:9][CH3:10])[CH2:6][CH2:7][OH:8])[CH3:4].Br[CH2:12][C:13]1[N:18]=[C:17]([CH2:19][O:20][C:21]2[CH:42]=[CH:41][C:24]([C:25]([NH:27][C:28]3[CH:29]=[C:30]([CH:37]=[CH:38][C:39]=3[CH3:40])[C:31]([NH:33][CH:34]3[CH2:36][CH2:35]3)=[O:32])=[O:26])=[CH:23][CH:22]=2)[CH:16]=[CH:15][CH:14]=1>CC(N(C)C)=O>[CH:34]1([NH:33][C:31](=[O:32])[C:30]2[CH:37]=[CH:38][C:39]([CH3:40])=[C:28]([NH:27][C:25](=[O:26])[C:24]3[CH:41]=[CH:42][C:21]([O:20][CH2:19][C:17]4[CH:16]=[CH:15][CH:14]=[C:13]([CH2:12][O:8][CH2:7][CH2:6][N:5]([CH2:9][CH3:10])[CH2:3][CH3:4])[N:18]=4)=[CH:22][CH:23]=3)[CH:29]=2)[CH2:35][CH2:36]1

Komponenten

5

Edukt 3

HCID 7497DiethylethanolamineHCID 24758Sodium hydrideHCID 666308713-[(4-{[6-(bromomethyl)pyridin-2-yl]methoxy}benzoyl)amino]-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 11387008N-cyclopropyl-3-({4-[(6-{[2-(diethylamino)ethoxy]methyl}pyridin-2-yl)methoxy]benzoyl}amino)-4-methylbenzamideAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

To a 60% dispersion of NaH in mineral oil (25 mg, 0.625 mmol) in DMA (4 mL) was added N,N-diethylethanolamine (24 mg, 0.205 mmol). The reaction was stirred at room temperature for 20 minutes. A solution of 3-[(4-{[6-(bromomethyl)pyridin-2-yl]methoxy}benzoyl)amino]-N-cyclopropyl-4-methylbenzamide (77 mg, 0.155 mmol) in DMA (2 mL) was added dropwise to the reaction which was then stirred for 1 h at room temperature. The reaction was quenched by the addition of water (1 mL) and was purified by preparative HPLC to give the title compound as a white solid (29 mg, 35%); NMR Spectrum: (DMSOd6) 0.58 (m, 2H), 0.69 (m, 2H), 0.96 (t, 6H), 2.26 (s, 3H), 2.50 (m, 4H), 2.64 (t, 2H), 2.86 (m, 1H), 3.59 (t, 2H), 4.59 (s, 2H), 5.75 (s, 2H), 7.18 (d, 2H), 7.33 (d, 1H), 7.42 (m, 2H), 7.64 (dd, 1H), 7.80 (s, 1H), 7.87 (t, 1H), 7.96 (d, 2H), 8.36 (d, 1H), 9.83 (s, 1H); Mass Spectrum: M+H+ 531.

Aufarbeitung

  1. stirringwas then stirred for 1 h at room temperature
  2. customThe reaction was quenched by the addition of water (1 mL)
  3. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a003fb90df5240e0b7664d06ed3905cb
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943776B2

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