Potassium Carbonate → (S)-N-(alpha-ethylbenzyl)-3-(aminocarbonylmethoxy)-2-phenyquinoline-4-carboxamide

HRID 651060

Reaktionsgleichung

Reaktionsgleichung von HRID 651060
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][C:38]([NH2:40])=[O:39]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:37][C:38]([NH2:40])=[O:39])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 5311424Talnetant

Produkt 1

HCID 10836803(S)-N-(alpha-ethylbenzyl)-3-(aminocarbonylmethoxy)-2-phenyquinoline-4-carboxamideAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.5 g (1.3 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1) were dissolved, under nitrogen atmosphere and magnetic stirring, in 5 ml of THF; 0.5 g (3.6 mmol) of K2CO3, 0.27 g (1.9 mmol) of 2-bromoacetamide and a small amount of KI were added. The reaction mixture was left overnight under magnetical stirring; the precipitate was filtered off and the residue dissolved in H2O and extracted with EtOAc; the organic layer was washed with sat. sol. NaCl, dried over Na2SO4 and evaporated in-vacuo to dryness. The crude product was triturated with hexane and then recrystallized form EtOH to yield 0.29 g of the title compound as a white solid.

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. dissolutionthe residue dissolved in H2O
  3. extractionextracted with EtOAc
  4. washthe organic layer was washed with sat. sol. NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated in-vacuo to dryness
  7. customThe crude product was triturated with hexane
  8. customrecrystallized form EtOH

Quellen und Nachweise

ORD-Eintrag
ord-90f4780e25824ab4a8893ba2340a036b
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277862B1

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