Trifluoroacetic acid → HCID 66710870、化合物

HRID 2089937ノート

反応式

HRID 2089937 の反応式
[N:1]1([CH:10]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:11]2[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[N:12]=2)C2C=CC=CC=2[N:3]=[N:2]1.[N-]=[N+]=[N-].[Na+].FC(F)(F)C(O)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:29]1([N:28]2[C:10]([C:11]3[C:16](=[O:17])[CH:15]=[CH:14][N:13]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[N:12]=3)=[N:1][N:2]=[N:3]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

参加物

7

反応物 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 86673246HCID 86673246、化合物

生成物 1

HCID 66710870HCID 66710870、化合物収率 56%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-[1H-benzotriazol-1-yl(phenylamino)methyl]-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.094 g, 0.20 mmol), sodium azide (0.030 g, 0.46 mmol), and tetrabutylammonium bromide (0.015 g, 0.047 mmol) in methylene chloride (5 mL) and water (5 mL) was treated with trifluoroacetic acid (0.040 mL, 0.52 mmol) and stirred 24 h at room temperature. After that time, the organic layer was separated and the aqueous layer was extracted with methylene chloride (3×25 mL). The combined organic extracts were washed with saturated NaCl aqueous solution (50 mL), dried (MgSO4), and concentrated. The crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate) to give an off-white solid that was recrystallized from ethyl acetate/hexanes to give 0.034 g (56%) of 3-(1-phenyl-1H-tetrazol-5-yl)-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one as colorless crystals.

後処理

  1. customAfter that time, the organic layer was separated
  2. extractionthe aqueous layer was extracted with methylene chloride (3×25 mL)
  3. washThe combined organic extracts were washed with saturated NaCl aqueous solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product purified by flash column chromatography (silica gel, 80:20 hexanes/ethyl acetate to ethyl acetate)
  7. customto give an off-white solid
  8. customthat was recrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-b5527230649b4a8799d90a31b0d00e13
出典データセット
uspto-grants-2013_05
特許番号
US08435995B2

反応ノート

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