Phosphorus sulfide (P2S5) → 4-[5-Fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-thiocarboxamide

HRID 1108079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108079
[F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2([C:14]([NH2:16])=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:32].C(=O)(O)[O-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[CH:5]=[C:6]([C:8]2([C:14](=[S:32])[NH2:16])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 9931329CJ-13454

Produkt 1

HCID 187863764-[5-Fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-thiocarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a stirred solution of 4-[5-fluoro-3-[4-(2-methylimidazol-1-yl)benzyloxy]-phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide (Example 5) in THF (10 ml) was added phosphorus pentasulfide (236 mg, 0.53 mmol) and sodium bicarbonate (176 mg, 2.1 mmol). The resulting mixture was heated at 40° C. for 4 hr. The mixture was concentrated in vacuo. To the residue was added water (100 ml) and the mixture was extracted with dichloromethane (2×100 ml). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified on column chromatography (LiChropprep --NH2) and then by p-TLC eluting with dichloromethane-methanol (10:1) to afford 38 mg of the titled compound as white solids.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added water (100 ml)
  3. extractionthe mixture was extracted with dichloromethane (2×100 ml)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on column chromatography (LiChropprep --NH2)
  7. washby p-TLC eluting with dichloromethane-methanol (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-bb3c1d7dacd74fa08bf53b5505a4a60b
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06063928

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