Diisopropylethylamine → 2-(Cyclopropylsulfonyl)-3-{[4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]carbonyl}-6-(trifluoromethyl)pyridine

HRID 1873841ノート

反応式

HRID 1873841 の反応式
[CH3:1][C:2]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:6])=[O:5])[CH3:3].[CH:23]1([S:26]([C:29]2[N:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[CH:34][C:30]=2[C:31](O)=[O:32])(=[O:28])=[O:27])[CH2:25][CH2:24]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>[NH4+].[Cl-].CN(C)C=O>[CH:23]1([S:26]([C:29]2[C:30]([C:31]([N:20]3[CH2:21][CH2:22][CH:17]([C:2]([CH3:1])([S:4]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=4)(=[O:5])=[O:6])[CH3:3])[CH2:18][CH2:19]3)=[O:32])=[CH:34][CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[N:37]=2)(=[O:27])=[O:28])[CH2:25][CH2:24]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidineHCID 684877982-(Cyclopropylsulfonyl)-6-(trifluoromethyl)nicotinic acid

生成物 1

HCID 252557852-(Cyclopropylsulfonyl)-3-{[4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]carbonyl}-6-(trifluoromethyl)pyridine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

実験手順

To a 50 ml round bottom flask was added 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine (1.64 g, 4.88 mmol), 2-(cyclopropylsulfonyl)-6-(trifluoromethyl)nicotinic acid (1.2 g, 4.06 mmol), Bop reagent (2.16 g, 4.88 mmol), diisopropylethyl amine (1.42 ml, 8.13 mmol) and 10 ml dimethylformamide. The resulting solution was stirred at room temperature 10 minutes. It was diluted with 60 ml NH4Cl solution and extracted with 60 ml ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated. The sesidue was purified on silica gel column eluted with 2:1 ethyl acetate/hexane. The desired fraction was collected and concentrated. The residue was further purified on prep-TLC to give title compound as a white solid.

後処理

  1. extractionextracted with 60 ml ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe sesidue was purified on silica gel column
  6. washeluted with 2:1 ethyl acetate/hexane
  7. customThe desired fraction was collected
  8. concentrationconcentrated
  9. customThe residue was further purified on prep-TLC

出典と根拠

ORDレコード
ord-f51855d3f41243778c9704316ca560cd
出典データセット
uspto-grants-2012_11
特許番号
US08304434B2

反応ノート

読み込み中…