Hydrochloric Acid → 3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol

HRID 609643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 609643
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12]N)=[CH:8][CH:7]=2)[CH:5]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.Cl>O1CCOCC1>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[C:10]3[C:9](=[CH:8][CH:7]=2)[NH:12][CH:19]=[C:18]3[CH2:17][CH2:16][CH2:15][OH:14])[CH:5]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 51624184-(4-hydrazinylphenyl)-4H-1,2,4-triazole

Produkt 1

HCID 106339143-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-olAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 4-(1,2,4-triazol-4-yl)phenylhydrazine (prepared as described in WO 94/03446, Example 1) (25 g, 143 mmol) in dioxan (250 ml) was treated with dihydropyran (24 g, 286 mmol) followed by 1 M hydrochloric acid (150 ml) and heated at reflux for 18 hours. The reaction mixture was evaporated with toluene then reevaporated. Inorganic solids were removed by treating the residue with a mixture of methanol and acetonitrile. The mother liquors were purified by column chromatography on silica using dichloromethane:methanol (9:1→4:1) as the eluant. The compound was recrystallised from acetonitrile to afford the title compound as a white solid (10.24 g, 30%), mp 205-207° C. δ (360 MHz, d6 -DMSO) 1.81 (2H, quintet, J=7Hz, CH2), 2.75 (2H, t, J=8Hz, CH2), 3.46 (2H, dt, J1 =6Hz, J2 =5Hz, CH2), 4.43 (1H, t, J=5Hz, OH), 7.26 (1H, d, J=2Hz, AR--H), 7.29 (1H, dd, J1 =9Hz, J2 =2Hz, Ar--H), 7.47 (1H, d, J=9Hz, Ar--H), 7.77 (1H, d, J=2Hz, Ar--H), 9.01 (2H, s, Triazole-H), 11.05 (1H, br s, indole NH). MS, CI+, m/z for (M+H)+ =243.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. customThe reaction mixture was evaporated with toluene
  4. customthen reevaporated
  5. customInorganic solids were removed
  6. additionby treating the residue
  7. additionwith a mixture of methanol and acetonitrile
  8. customThe mother liquors were purified by column chromatography on silica
  9. customThe compound was recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-0e5949a4c40a4d3d97df482c0c84c31c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998415

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