Triethylamine → HCID 86680845, compound

HRID 60574

Reaction equation

HRID 60574 reaction equation
[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

Participants

7

Reactant 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

Product 1

HCID 86680845HCID 86680845, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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: water/acetonitrile (containing 0.1% TFA))
  7. concentrationthe 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

Sources & evidence

ORD record
ord-5af5c77c225946ed9fec98afe25ae031
Source dataset
uspto-grants-2016_09
Patent number
US09440990B2

Linked notes

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