Ethyl Acetate → 4-[6-(2,6-Diethyl-phenyl)-3-(2,2-dimethyl-morpholin-4-ylmethyl)-2-methyl-pyridin-4-yloxy]-2-hydroxy-benzamide

HRID 1392674

Reaktionsgleichung

Reaktionsgleichung von HRID 1392674
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:16][CH3:17])[N:5]=[C:4]([CH3:18])[C:3]=1[CH2:19][N:20]1[CH2:25][CH2:24][O:23][C:22]([CH3:27])([CH3:26])[CH2:21]1.[OH:28][C:29]1[CH:37]=[C:36]([OH:38])[CH:35]=[CH:34][C:30]=1[C:31]([NH2:33])=[O:32].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN1CCCC1=O.[Cu].O>[CH2:16]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH2:14][CH3:15])[C:8]=1[C:6]1[N:5]=[C:4]([CH3:18])[C:3]([CH2:19][N:20]2[CH2:25][CH2:24][O:23][C:22]([CH3:27])([CH3:26])[CH2:21]2)=[C:2]([O:38][C:36]2[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[C:29]([OH:28])[CH:37]=2)[CH:7]=1)[CH3:17]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 766012,4-DihydroxybenzamideHCID 596782124-[4-Chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine

Produkt 1

HCID 596782004-[6-(2,6-Diethyl-phenyl)-3-(2,2-dimethyl-morpholin-4-ylmethyl)-2-methyl-pyridin-4-yloxy]-2-hydroxy-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-[4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine (30 mg, 0.08 mmol), 2,4-dihydroxy-benzamide (24 mg, 0.16 mmol), copper powder (10 mg) and K2CO3 (22 mg, 0.16 mmol) in 1-methyl-2-pyrrolidinone (1 mL) is heated at 150° C. overnight. After cooling, EtOAc (10 mL) and water (10 mL) are added to the mixture. The organic layer is separated, washed with brine (3×), dried (Na2SO4) and concentrated. The crude is purified by PTLC (1:1 Hexane/EtOAc) to give to give the title compound. 1H NMR (CDCl3) 12.41 (s, 1H), 7.35 (d, 2H), 7.23 (m, 1H), 7.10 (m, 2H), 6.63 (s, 1H), 6.51 (m, 2H), 5.85 (br, 2H), 3.72 (m, 2H), 3.56 (s, 2H), 2.74 (s, 3H), 2.41-2.30 (m, 6H), 1.20 (s, 6H), 1.76 (m, 2H), 1.01 (t, 6H).

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe organic layer is separated
  3. washwashed with brine (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude is purified by PTLC (1:1 Hexane/EtOAc)
  7. customto give

Quellen und Nachweise

ORD-Eintrag
ord-eca786cb8079415dbb54b6a3d0fcdd7b
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342115B2

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