Water → {[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]amino}-acetic acid methyl ester

HRID 1698183

Reaktionsgleichung

Reaktionsgleichung von HRID 1698183
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[N:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH2:37].O>CN(C=O)C.C(=O)(O)[O-].[NH4+]>[CH3:33][O:34][C:35](=[O:38])[CH2:36][NH:37][C:17]([C:16]1[C:11]2[CH:10]=[N:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:12]=2[CH:13]=[N:14][CH:15]=1)=[O:19]

Komponenten

7

Edukt 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 122755Glycine methyl ester hydrochlorideHCID 592781371-(4-Fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid

Produkt 1

HCID 66727434{[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]amino}-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 14013Ammonium BicarbonateLösungsmittel

Versuchsvorschrift

A suspension of 1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carboxylic acid (2.95 g, 11.5 mmol) in DMF (25 mL) was treated with CDI (1.51 g, 12.0 mmol). The mixture turned to a dark brown clear solution in 5 minutes, and then a solid precipitate formed. Additional DMF (10 mL) was added to assist stirring. The mixture was stirred for 1 hour. A solution of glycine methyl ester hydrochloride (2.42 g, 14.9 mmol) in DMF (5 mL) was added. After 18 hours, the mixture was poured into water (200 mL) and diluted with saturated aqueous ammonium bicarbonate (50 mL). The solid was collected by filtration to afford {[1-(4-fluorophenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-acetic acid methyl ester as a light brown solid.

Aufarbeitung

  1. customa solid precipitate formed
  2. stirringThe mixture was stirred for 1 hour
  3. waitAfter 18 hours
  4. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0df625fb00704751998d245e16b6ae2c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163918B2

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