Isopropanol → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline

HRID 7475

Reaktionsgleichung

Reaktionsgleichung von HRID 7475
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[N:5][CH:4]=1.[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH2:28])=[C:26]([F:32])[CH:25]=1.C(O)(C)C>CC(O)CCC>[Cl:23][C:24]1[C:30]([OH:31])=[CH:29][C:27]([NH:28][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[N:5][CH:4]=2)=[C:26]([F:32])[CH:25]=1

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 1586545-Amino-2-chloro-4-fluorophenolHCID 219910114-Chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride

Produkt 1

HCID 219910264-(4-Chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 223862-PentanolLösungsmittel

Versuchsvorschrift

A suspension of 4-chloro-6-methoxy-7-(4-pyridylmethoxy)cinnoline hydrochloride (0.17 g, 0.45 mmol) and 4-chloro-2-fluoro-5-hydroxyaniline (102 mg, 0.63 mmol), (prepared as described in EP 061741 A2), in 2-pentanol (3.5 ml) was heated at reflux overnight. After cooling, isopropanol was added. The solid formed was filtered off, washed with isopropanol, ether and dried under vacuum to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxy-7-(4-pyridylmethoxy)cinnoline as the hydrochloride salt (yellow solid, 194 mg, 86%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customThe solid formed
  5. filtrationwas filtered off
  6. washwashed with isopropanol, ether
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0d9c8fe8bd4f4677b9f2be711a09a26f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087602B2

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