Dimethylformamide → 4-(3-Amino-4-cyano-pyrazol-1-ylmethyl)-benzoic acid methyl ester

HRID 416238

Reaktionsgleichung

Reaktionsgleichung von HRID 416238
[NH2:1][C:2]1[C:6]([C:7]#[N:8])=[CH:5][NH:4][N:3]=1.CN(C=O)C.[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1>CCOCC.CC(C)=O>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:4]2[CH:5]=[C:6]([C:7]#[N:8])[C:2]([NH2:1])=[N:3]2)=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178510443HCID 178510443, Verbindung

Produkt 1

HCID 666222814-(3-Amino-4-cyano-pyrazol-1-ylmethyl)-benzoic acid methyl esterAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584533Acetone diethyletherLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-1H-pyrazole-4-carbonitrile (1.211 g, 11.21 mmol) in anhydrous DMF (20 ml) K2CO3 (5.414 g, 39.24 mmol) was added. The suspension was stirred 5 min at room temperature and treated with p-bromomethylbenzoic acid methyl ester (2.568 g, 11.21 mmol), stirred for 2.5 hrs at 100° C., cooled and filtered. Filtrate was evaporated to form an oily residue, which was dissolved in a mixture Et2O-acetone and kept overnight at −10° C. A crystalline material was formed which was triturated with hot EtOAc, again kept overnight at −10° C. and was collected by filtration to form the title compound 95 (675 mg, 24% yield). LRMS: 256.3 (calc.), 257.3 (found).

Aufarbeitung

  1. stirringstirred for 2.5 hrs at 100° C.
  2. temperaturecooled
  3. filtrationfiltered
  4. customFiltrate was evaporated
  5. customto form an oily residue, which
  6. waitkept overnight at −10° C
  7. customA crystalline material was formed which
  8. customwas triturated with hot EtOAc, again kept overnight at −10° C.
  9. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-89e0ff38368243da9265131a386cdc01
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088805B2

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