Methyl iodide → 4-(3-Bromo-4-fluorophenyl)-3-[4-(methylamino)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one

HRID 82725ノート

反応式

HRID 82725 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][C:21](=O)C(F)(F)F)=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[C:16]([NH:20][CH3:21])=[N:17][O:18][N:19]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

7

反応物 3

HCID 6328Methyl iodide2 回HCID 11430Potassium CarbonateHCID 58755133N-[4-[4-(3-Bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl]-2,2,2-trifluoroacetamide

生成物 1

HCID 585582554-(3-Bromo-4-fluorophenyl)-3-[4-(methylamino)-1,2,5-oxadiazol-3-yl]-1,2,4-oxadiazol-5(4H)-one収率 84.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of N-{4-[4-(3-bromo-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-2,2,2-trifluoroacetamide (0.59 mg, 1.3 mmol) in N,N-dimethylformamide (3 mL) was treated with potassium carbonate (0.28 g, 2.0 mmol) followed by methyl iodide (125 μL, 2 mmol) and stirred for 2 h. The reaction mixture was treated with additional methyl iodide (200 μL, 3.2 mmol) and stirred for 16 h. The reaction mixture was diluted with water (100 mL) and brine (25 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with water (3×100 mL) and brine (100 mL), dried with sodium sulfate, filtered, and concentrated to a crude residue which was purified by silica gel to give the desired product (0.39 g, 81%).

後処理

  1. stirringstirred for 16 h
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washThe combined organic extracts were washed with water (3×100 mL) and brine (100 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a crude residue which
  7. customwas purified by silica gel

出典と根拠

ORDレコード
ord-1100fdf485b64ca19de66543dcf9c3f0
出典データセット
uspto-grants-2014_09
特許番号
US08846726B2

反応ノート

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