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 1784499

反応式

HRID 1784499 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of the acid (7-C) (138.9 mg, 0.439 mmol) 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.

後処理

  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

出典と根拠

ORDレコード
ord-09ebaf0ff92f45e8b1338251305a7176
出典データセット
uspto-grants-2009_03
特許番号
US07504402B2

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