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Water → Ethyl 2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-(pyrimidin-5-yl)propanoate

HRID 923466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 923466
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16](O)=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.ClC(N(C)C)=C(C)C.[NH2:32][C:33]([C:40]1[CH:41]=[N:42][CH:43]=[N:44][CH:45]=1)([CH3:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35].O>ClCCl.C(N(CC)CC)C>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:32][C:33]([C:40]3[CH:45]=[N:44][CH:43]=[N:42][CH:41]=3)([CH3:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1
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Komponenten

7

Edukt 4

HCID 962WaterHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 118308755Ethyl 2-amino-2-(pyrimidin-5-yl)propanoate

Produkt 1

HCID 90192599Ethyl 2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-(pyrimidin-5-yl)propanoate
Ausbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a mixture of 167 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid and 1.5 ml of dichloromethane was added 90 μl of 1-chloro-N,N,2-trimethylprop-1-en-1-amine under ice-cooling, followed by stirring at room temperature for 30 minutes. A solution of 93 mg of ethyl 2-amino-2-(pyrimidin-5-yl)propanoate in 1.5 ml of dichloromethane and 0.15 ml of triethylamine were added thereto under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 56 mg of ethyl 2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-(pyrimidin-5-yl)propanoate.

Aufarbeitung

  1. temperaturecooling
  2. temperatureunder ice-cooling
  3. stirringby stirring at room temperature for 2 hours
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customthe solvent was then evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bc45c0abea1d4f6597de33f061d62722
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09278968B2

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