2-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylate → HCID 86665900, Verbindung

HRID 75443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75443
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([Cl:15])[N:12]=[C:11]([NH:16][CH:17]([CH3:19])[CH3:18])[C:10]=1[NH2:20])[CH2:2]2.[CH3:21][N:22]([CH3:28])[CH2:23][CH2:24][C:25]([O-])=[O:26].CN(C)CCC(O)=O.C(OC1C=CC2C(=CC=CC=2)N1C(OCC(C)C)=O)C(C)C>CN(C)C=O>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[C:10]([NH:20][C:25](=[O:26])[CH2:24][CH2:23][N:22]([CH3:28])[CH3:21])=[C:11]([NH:16][CH:17]([CH3:18])[CH3:19])[N:12]=[C:13]([Cl:15])[N:14]=1)[CH2:2]2

Komponenten

5

Edukt 3

HCID 1006212-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylateHCID 2398283-(Dimethylamino)propanoic acidHCID 866658986-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N4-isopropylpyrimidine-4,5-diamine 3-(dimethylamino)propanoate

Produkt 1

HCID 86665900HCID 86665900, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-N4-isopropylpyrimidine-4,5-diamine 3-(dimethylamino)propanoate (48, 0.500 g, 1.68 mmoles) was dissolved in dimethylformamide and 3-dimethylaminopropionic acid (0.310 g, 2.02 mmoles) and isobutyl 2-isobutoxyquinoline-1(2H)-carboxylate (IIDQ, 0.699 mL, 2.35 mmoles) were added. The reaction mixture was allowed to stir at room temperature for 18 hours, concentrated, and purified by silica gel column chromatography (5-10% ethanol in dichloromethane) to provide N-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-2-chloro-6-(isopropylamino)pyrimidin-5-yl)-3-(dimethylamino)propanamide (49) as a tan solid. Yield: 0.350 g (53%). LCMS (Waters walk-on); 2.43 min., 397.2, M+H.

Aufarbeitung

  1. concentrationconcentrated
  2. custompurified by silica gel column chromatography (5-10% ethanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-42c657b2116546b7ac7fbea5dd8ed065
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835429B2

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