Triethylamine → 3-(4-Fluorophenyl)-5-(4-{5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo [2.2.2]oct-1-yl)-1,2,4-oxadiazole

HRID 22847

반응식

HRID 22847 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]34[CH2:20][CH2:19][C:16]([C:21](O)=[O:22])([CH2:17][CH2:18]3)[CH2:15][CH2:14]4)[O:10][N:9]=2)=[CH:4][CH:3]=1.[F:24][C:25]([F:37])([F:36])[C:26]1[CH:35]=[CH:34][CH:33]=[CH:32][C:27]=1[C:28]([NH:30][NH2:31])=O.[Cl-].ClC1N(C)CC[NH+]1C.C(N(CC)CC)C>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[C:11]([C:13]34[CH2:20][CH2:19][C:16]([C:21]5[O:22][C:28]([C:27]6[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=6[C:25]([F:24])([F:36])[F:37])=[N:30][N:31]=5)([CH2:15][CH2:14]3)[CH2:17][CH2:18]4)[O:10][N:9]=2)=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 27774152-(Trifluoromethyl)benzoic acid hydrazideHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 225917214-[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]bicyclo[2.2.2]octane-1-carboxylic acid

생성물 1

HCID 225916773-(4-Fluorophenyl)-5-(4-{5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo [2.2.2]oct-1-yl)-1,2,4-oxadiazole

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of the acid (7-C) (138.9 mg, 0.439 nmol) and 2-(trifluoromethyl)benzoic hydrazide (7-D) (89.7 mg, 0.439 mmol) was first co-evaporated with toluene three times. Dichloromethane (7 mL) was added to the mixture as solvent. To the resulting suspension was added 2-chloro-1,3-dimethylimidazolinium chloride (743 mg, 4.39 mmol) followed by triethylamine (1.2 mL, 8.78 mmol). The mixture was allowed to stir at room temperature under nitrogen for 48 h to ensure the completion of the reaction. The reaction mixture was then diluted with dichloromethane, washed with water, 1N HCl, saturated sodium bicarbonate aqueous solution, and lastly brine. The organics were dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography using hexane/ethyl acetate (3/1) as eluent to give 3-(4-fluorophenyl)-5-(4-{5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo[2.2.2]oct-1-yl)-1,2,4-oxadiazole (7-E) as a white solid. 1H NMR (500 MHz, CDCl3) δ 2.25 (s, 12H), 7.21 (t, J=8.7 Hz, 2H), 7.74-7.76 (m, 2H), 7.91 (m, 1H), 8.11-8.15 (m, 3H) ppm. ESI-MS m/z (M+H) 485.2.

후처리

  1. customthe completion of the reaction
  2. washwashed with water, 1N HCl, saturated sodium bicarbonate aqueous solution, and lastly brine
  3. dry with materialThe organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-eb28e951aa594c0495e3315f21b6e3bf
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849636B2

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