Citric Acid → Ethyl 4-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 57709

Reaktionsgleichung

Reaktionsgleichung von HRID 57709
Cl[C:2]1[C:3]2[N:4]([N:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:18]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])[N:7]=1.Cl.Cl.[NH2:26][CH2:27][CH2:28][NH:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][N:31]=1.C(N(CC)C(C)C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.C(OCC)(=O)C>[C:34]([C:33]1[CH:36]=[CH:37][C:30]([NH:29][CH2:28][CH2:27][NH:26][C:2]2[C:3]3[N:4]([N:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:18]=3)[CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=3[Cl:15])[N:7]=2)=[N:31][CH:32]=1)#[N:35]

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 81531DiisopropylethylamineHCID 58170012HCID 58170012, VerbindungHCID 669113296-[(2-Aminoethyl)amino]nicotinonitrile dihydrochloride

Produkt 1

HCID 25168329Ethyl 4-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

1 g (5 mmol) of ethyl 4-chloro-6-(2,4-dichlorophenyl)pyrazolo[1,5-a]pyrazine-2-carboxylate (Example 12A) was initially charged in 15 ml of dry DMSO, and 1.55 g (4.22 mmol) of 6-[(2-aminoethyl)amino]nicotinonitrile dihydrochloride (Example 2A) and 5.8 ml (33.5 mmol) of N,N-diisopropylethylamine were added and the mixture was heated in a microwave at 150° C. for 30 min. Ethyl acetate and 10% strength citric acid were added, and the reaction mixture was extracted. The organic phase was washed with sodium chloride solution and dried over magnesium sulfate. This gave, after concentration, 1.4 g (70% of theory) of the product as a solid.

Aufarbeitung

  1. extractionthe reaction mixture was extracted
  2. washThe organic phase was washed with sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThis gave, after concentration, 1.4 g (70% of theory) of the product as a solid

Quellen und Nachweise

ORD-Eintrag
ord-e54d1e8586404cc6a937f46b7d088ebf
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434731B2

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