4-Bromoaniline → Ethyl 4'-[(5-Ethylpyrazolo[1,5-a]pyrimidine-7-yl)amino]biphenyl-2-carboxylate

HRID 1450378

Reaktionsgleichung

Reaktionsgleichung von HRID 1450378
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH3:12])[CH:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][CH:15]=1.BrC1C=CC(N)=CC=1.BrC1C=CC=CC=1C(OCC)=O>C(O)C>[CH2:11]([C:4]1[CH:3]=[C:2]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:18][CH:19]=2)[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 78074-BromoanilineHCID 80186Ethyl 2-bromobenzoateHCID 105354107-Chloro-5-ethylpyrazolo[1,5-a]pyrimidineHCID 19975704Ethyl 4'-amino-biphenyl-2-carboxylate

Produkt 1

HCID 19975762Ethyl 4'-[(5-Ethylpyrazolo[1,5-a]pyrimidine-7-yl)amino]biphenyl-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 800 mg (4.4 mmol) 7-chloro-5-ethylpyrazolo[1,5-a]pyrimidine (Example 1, Step B) and 1.0 g (4.1 mmol) ethyl 4'-amino-biphenyl-2-carboxylate (prepared from protected 4-bromoaniline and ethyl 2-bromobenzoate by the method of J. C. Adrian, Jr., C. S. Wilcox, J. Am. Chem. Soc. 1989, 111, 8055) in 40 ml dry ethanol was heated with reflux for 5 h. After cooling to room temperature pale yellow crystals of the title compound precipitated, which were filtered by suction and recrystallized from ethanol, m.p. 223°-225° C.

Aufarbeitung

  1. temperaturewith reflux for 5 h

Quellen und Nachweise

ORD-Eintrag
ord-4499175f94414b4aa9171766f50c1ecd
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602137

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