Water → HCID 19603815, Verbindung

HRID 1604703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1604703
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[C:14]([OH:16])=[O:15].[C:17]([C:21]1[N:22]=[C:23]([C:26]2[O:27][C:28]3[CH:34]=[CH:33][C:32]([CH2:35]Cl)=[CH:31][C:29]=3[CH:30]=2)[S:24][CH:25]=1)([CH3:20])([CH3:19])[CH3:18].O>CN(C)C=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:35][C:32]1[CH:33]=[CH:34][C:28]3[O:27][C:26]([C:23]4[S:24][CH:25]=[C:21]([C:17]([CH3:19])([CH3:18])[CH3:20])[N:22]=4)=[CH:30][C:29]=3[CH:31]=1)[N:9]=[C:8]2[C:14]([OH:16])=[O:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 103753065-methoxy-1H-indazole-3-carboxylic acidHCID 19603727HCID 19603727, Verbindung

Produkt 1

HCID 19603815HCID 19603815, VerbindungAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Sodium hydride (60% in mineral oil, 7.79 g) was added into a solution of 5-methoxy-1H-indazole-3-carboxylic acid (17.0 g) in N,N-dimethylformamide (400 ml) at room temperature under nitrogen atmosphere. After 30 minutes, 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (29.76 g) was added to the solution over 5 minutes. After being stirred continuously for 3 hours at 45° C., the reaction mixture was poured into water (2 l) and the reaction vessel was washed with water (200 ml). After combining the washing mixture to the aqueous mixture, the resulting mixture was made acidic with 10% hydrochloric acid aqueous solution (500 ml) and stirred vigorously for one hour. The precipitate was collected by filtration, washed with water and air-dried for one day. The crude product was washed with a mixture of isopropyl alcohol and isopropylethyl ether (7:3) and dried in vacuo to give 5-methoxy-1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indazole-3-carboxylic acid (36.5 g).

Aufarbeitung

  1. washthe reaction vessel was washed with water (200 ml)
  2. stirringstirred vigorously for one hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customair-dried for one day
  6. washThe crude product was washed with a mixture of isopropyl alcohol and isopropylethyl ether (7:3)
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-733af9862d9649bcaca1acf6c819ccc0
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05994378

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