Hydrochloric Acid → 4-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline hydrochloride

HRID 1057341

Reaktionsgleichung

Reaktionsgleichung von HRID 1057341
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[N:17]=[C:18]([CH3:21])[S:19][CH:20]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1.[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH2:25].Cl>CC(O)CCC.C(O)(C)C>[ClH:1].[F:22][C:23]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:24]=1[NH:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[N:17]=[C:18]([CH3:21])[S:19][CH:20]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 101540985-Amino-4-fluoro-2-methylphenolHCID 219910614-Chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline

Produkt 1

HCID 219910284-(2-Fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline hydrochlorideAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 223862-PentanolLösungsmittel

Versuchsvorschrift

A suspension of 4-chloro-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline (150 mg, 0.46 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (78 mg, 0.56 mmol), (prepared as described for the starting material in Example 11), in 2-pentanol (3 ml) and a 5M solution of hydrogen chloride in isopropanol (105 μl) was heated at reflux for 90 minutes. The solid obtained was filtered off, washed with isopropanol followed by ether to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6-methoxy-7-[(2-methylthiazol-4-yl)methoxy]cinnoline hydrochloride as a pale yellow solid (190 mg, 82%).

Aufarbeitung

  1. custom(prepared
  2. temperatureat reflux for 90 minutes
  3. customThe solid obtained
  4. filtrationwas filtered off
  5. washwashed with isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-4783bb1bc2b7418096c3ac2ef95bd9db
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514971B1

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