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

HRID 609643노트

반응식

HRID 609643 반응식
[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

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 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-0e5949a4c40a4d3d97df482c0c84c31c
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998415

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