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Sodium Carbonate → 7-[3-(Dimethylamino)propoxy]-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

HRID 1415147
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1415147
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].C([Li])CCC.Cl[C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:25])[N:17]=[C:16]2[N:26]([CH3:29])[CH:27]=[N:28][C:15]=12.C(=O)([O-])[O-].[Na+].[Na+]>CCCCCC.C1C=CC=CC=1>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][O:6][C:14]1[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:18]([CH3:25])[N:17]=[C:16]2[N:26]([CH3:29])[CH:27]=[N:28][C:15]=12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 766463-(Dimethylamino)-1-propanolHCID 123876407-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid ethyl esterHCID 178418339Butyllithium

Produkt 1

HCID 123876447-[3-(Dimethylamino)propoxy]-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 1.1 g. of 3-dimethylaminopropan-1-ol in 100 ml. of dry benzene are added 4 ml. of a 20% solution of butyl lithium in hexane. The mixture is stirred at room temperature for 15 minutes. After this time, 2.5 g. of 7-chloro-3,5-dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester are added and the solution is heated at reflux temperature with stirring for 12 hours. After cooling, the solution is shaken with 50 ml. of a saturated aqueous sodium carbonate solution. The benzene layer is separated, dried with calcium chloride and evaporated to dryness. The remaining oily residue, 7-[3-(dimethylamino)propoxy]-3,5 -dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, is purified by distillation, yield 2.2 g. (85%); b.p. 175°-180° /0.01 mm.

Aufarbeitung

  1. temperaturethe solution is heated
  2. temperatureat reflux temperature
  3. stirringwith stirring for 12 hours
  4. temperatureAfter cooling
  5. stirringthe solution is shaken with 50 ml
  6. customThe benzene layer is separated
  7. dry with materialdried with calcium chloride
  8. customevaporated to dryness
  9. distillationThe remaining oily residue, 7-[3-(dimethylamino)propoxy]-3,5 -dimethyl-3H-imidazo[4,5-b]pyridine-6-carboxylic acid, ethyl ester, is purified by distillation, yield 2.2 g

Quellen und Nachweise

ORD-Eintrag
ord-2ba4b8ddd96d44cb86810fadaab0fbeb
Quelldatensatz
uspto-grants-1977_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04003908

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