p-Toluenesulfonic acid → HCID 178463003, Verbindung

HRID 923347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 923347
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([NH2:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25](=O)[CH2:26][C:27](OCC)=[O:28])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)[CH3:15].CC1C=CC(S(O)(=O)=O)=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]3[NH:13][C:11]4[N:10]([N:9]=[C:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[N:12]=4)[C:27](=[O:28])[CH:26]=3)=[CH:22][CH:23]=2)[CH:18]=[N:17]1)[CH3:15]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 90109086ethyl 3-(1-ethyl-1H-indazol-5-yl)-3-oxopropanoateHCID 1785082995-(4-fluorophenyl)-4H-1,2,4-triazol-3-amine

Produkt 1

HCID 178463003HCID 178463003, VerbindungAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 3-(4-fluorophenyl)-1H-1,2,4-triazol-5-amine (100 mg, 0.56 mmol) in diphenyl ether (1 ml) was added ethyl 3-(1-ethyl-1H-indazol-5-yl)-3-oxopropanoate (400 mg, 1.540 mmol) and TsOH (6 mg, 0.03 mmol), and the resulting mixture was strirred for 2.5 h at 170° C. The reaction mixture was then quenched by the addition of ethyl ether (8 ml). The solids were collected by filtration and washed with dichloromethane (5 ml) to afford 5-(1-ethyl-1H-indazol-5-yl)-2-(4-fluorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7(4H)-one as a light yellow solid (69 mg, 24%).

Aufarbeitung

  1. customThe reaction mixture was then quenched by the addition of ethyl ether (8 ml)
  2. filtrationThe solids were collected by filtration
  3. washwashed with dichloromethane (5 ml)

Quellen und Nachweise

ORD-Eintrag
ord-42c90e75eb5b45c9b2968eb767854450
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278973B2

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