Water → Pirmagrel

HRID 326144

Reaktionsgleichung

Reaktionsgleichung von HRID 326144
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[OH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[N:34]2[CH:35]=[N:36][CH:37]=[C:33]2[CH:32]=[CH:31][CH:30]=1.[OH2:38]>CN(C)C=O>[C:23]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[N:34]2[CH:35]=[N:36][CH:37]=[C:33]2[CH:32]=[CH:31][CH:30]=1)([OH:38])=[O:22]

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 132061465-(6-Hydroxyhexyl)-imidazo[1,5-a]pyridine

Produkt 1

HCID 55390Pirmagrel

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Pyridinium dichromate (0.94 g) is added as a solid to a solution of 5-(6-hydroxyhexyl)-imidazo[1,5-a]pyridine (123 mg) in 10 ml of N,N-dimethylformamide at 25° under nitrogen. The solution is stirred for 6 hours, poured into 150 ml of water and extracted with methylene chloride (5×20 ml). The organic extracts are washed with 1 N sodium hydroxide. Acidification of the aqueous phase to pH=6, extraction with methylene chloride and drying over sodium sulfate/magnesium sulfate yields 5-(5-carboxypentyl)-imidazo[1,5-a]pyridine of Example 2 melting at 145°-146°.

Aufarbeitung

  1. extractionextracted with methylene chloride (5×20 ml)
  2. washThe organic extracts are washed with 1 N sodium hydroxide
  3. extractionAcidification of the aqueous phase to pH=6, extraction with methylene chloride
  4. dry with materialdrying over sodium sulfate/magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-01c70a673aab45239c2a035f9aecd3d5
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04444775

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