Diisopropylethylamine → ethyl 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylate

HRID 1802249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1802249
[Br:1][C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:25])[C:21]=1[C:22](O)=[O:23])=[O:16])[CH3:13].CCCP(=O)=O.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:12]([O:14][C:15]([C:17]1[CH:18]=[N:19][N:20]([CH3:25])[C:21]=1[C:22](=[O:23])[NH:10][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([Br:1])[N:11]=[C:5]2[CH:6]=1)=[O:16])[CH3:13]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 677745572-Bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine

Produkt 1

HCID 67775496ethyl 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylateAusbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-amine (2.39 g, 11.2 mmol), 4-(ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (2.22 g, 11.2 mmol), propylphosphonic anhydride (50% in ethyl acetate, 16.5 ml, 28.0 mmol) and N,N-diisopropylethylamine (5.72 ml, 33.7 mmol) in tetrahydrofuran (80 ml) was refluxed for 18 hours under argon atmosphere. The solvent was evaporated and the resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water 4 times and dried in vacuo affording 5-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (3.64 g, 82.5%) as a light yellow solid. mp: 177-180° C., MS: m/z=393.0/395.0 (M+H+)

Aufarbeitung

  1. temperaturewas refluxed for 18 hours under argon atmosphere
  2. customThe solvent was evaporated
  3. customthe resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water 4 times
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-89a362b08e7e4e50b4380b5548f4dee0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349824B2

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