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

HRID 1459708노트

반응식

HRID 1459708 반응식
[CH:1]1[C:6]([NH:7]N)=[CH:5][CH:4]=[C:3]([N:9]2[CH:13]=[N:12][N:11]=[CH:10]2)[CH:2]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.Cl>O1CCOCC1>[N:12]1[N:11]=[CH:10][N:9]([C:3]2[CH:2]=[C:1]3[C:6](=[CH:5][CH:4]=2)[NH:7][CH:19]=[C:18]3[CH2:17][CH2:16][CH2:15][OH:14])[CH:13]=1

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of 4'-(1,2,4-triazol-4-yl)phenylhydrazine (25 g, 143 mmol) in dioxan (250 ml) was treated with dihydropyran (24 g, 286 mmol) followed by 1M hydrochloric acid (150 ml) and heated at reflux for 18 h. The reaction mixture was evaporated, treated with toluene then re-evaporated. 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 colourless solid (10.24 g, 30%); mp 205°-207° C. (Found: C, 64.37; H, 5.76; N, 22.83. C13H14N4O requires C, 64.45; H, 5.82; N, 23.13%.) δ (360 MHz, d6 -DMSO) 1.81 (2H, q, J=7 Hz, CH2), 2.75 (2H, t, J=8 Hz, CH2), 3.46 (2H, dt, J1 =6, J2 =5 Hz, CH2), 4.43 (1H, t, J=5 Hz, OH), 7.26 (1H, d, J=2 Hz, Ar--H), 7.29 (1H, dd, J1 =9, J2 =2 Hz, Ar--H), 7.47 (1H, d, J=9 Hz, Ar--H), 7.77 (1H, d, J=2 Hz, Ar--H), 9.01 (2H, s, triazole-H), 11.05 (1H, br s, indole NH). MS, CI+, m/z=243 for (M+H)+.

후처리

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

출처 및 근거

ORD 기록
ord-5444e45af06b4fb4a9a8f9bd6a917b03
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05854268

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