Methanol → HCID 178517843, Verbindung

HRID 1424408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424408
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[O:26]C(=O)O[C:23]2=O)=[CH:18][CH:17]=1.C[O-].[Na+].CO>C1COCC1>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([OH:26])[C:23]2[N:6]=[C:4]([OH:5])[C:3]3[C:2](=[CH:10][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:8][CH:7]=3)[N:1]=2)=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 697392-Amino-4-(trifluoromethyl)benzamideHCID 10942334Sodium MethoxideHCID 86649050HCID 86649050, Verbindung

Produkt 1

HCID 178517843HCID 178517843, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 2-amino-4-(trifluoromethyl)benzamide (840 mg, 4.16 mmol), in THF (15 mL) was added 5-(4-fluorophenyl)-1,3-dioxolane-2,4-dione from Example 16 (1225 mg, 6.24 mmol) and the mixture was heated at 50° C. for 4 h. The solvent was evaporated and the crude 2-(2-(4-fluorophenyl)-2-hydroxyacetamido)-4-(trifluoromethyl)benzamide was dissolved in MeOH (10 mL), added 0.5 M sodium methoxide in MeOH (2.5 mL, 1.25 mmol) and the reaction mixture was heated at 50° C. for 1 h. The solvent was evaporated and then 1N hydrochloric acid was added. The mixture was extracted with EtOAc and the organic phase was dried over sodium sulfate and concentrated in vacuo to afford crude 2-((4-fluorophenyl)(hydroxy)methyl)-7-(trifluoromethyl)quinazolin-4-ol, which was used in next reaction without purification. LC-MS (ESI) m/z 339 (M+Na)+.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe crude 2-(2-(4-fluorophenyl)-2-hydroxyacetamido)-4-(trifluoromethyl)benzamide was dissolved in MeOH (10 mL)
  3. temperaturethe reaction mixture was heated at 50° C. for 1 h
  4. customThe solvent was evaporated
  5. addition1N hydrochloric acid was added
  6. extractionThe mixture was extracted with EtOAc
  7. dry with materialthe organic phase was dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-692c830ec0e24b34b385893c2f8958e4
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927711B2

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