Triethylamine → (4-Benzyl-4-hydroxypiperidin-1-yl)(3-methyl-5-(pyridin-4-yl)-1,2-oxazol-4-yl)methanone

HRID 240374

反応式

HRID 240374 の反応式
[CH3:1][C:2]1[C:6]([C:7]([OH:9])=O)=[C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[O:4][N:3]=1.[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[CH2:16]([C:23]1([OH:29])[CH2:28][CH2:27][N:26]([C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:9])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 981524-Benzyl-4-piperidinolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 282757673-Methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid

生成物 1

HCID 86680845(4-Benzyl-4-hydroxypiperidin-1-yl)(3-methyl-5-(pyridin-4-yl)-1,2-oxazol-4-yl)methanone収率 62.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 3-methyl-5-(pyridin-4-yl)-1,2-oxazole-4-carboxylic acid (0.25 g), 4-benzyl-4-hydroxypiperidine (0.35 g), HATU (0.70 g) and triethylamine (0.85 mL) in DMF (5.0 mL) was stirred at room temperature for 3 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and then purified by preparative HPLC(C18, mobile phase: water/acetonitrile (containing 0.1% TFA)), and the obtained fraction was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.29 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. custompurified by preparative HPLC(C18, mobile phase
  7. concentrationwater/acetonitrile (containing 0.1% TFA)), and the obtained fraction was concentrated under reduced pressure
  8. additionTo the residue was added saturated aqueous sodium hydrogen carbonate solution
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialThe extract was dried over anhydrous sodium sulfate
  11. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-b0b798eea0d54ee49d2273620a0ec98b
出典データセット
uspto-grants-2014_02
特許番号
US08648079B2

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