Triethylamine → (4-(2,4-Difluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(1,3-oxazol-5-yl)phenyl)methanone

HRID 717308Notes

Reaction equation

HRID 717308 reaction equation
[O:1]1[C:5]([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=O)=[CH:4][N:3]=[CH:2]1.Cl.[F:16][C:17]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:18]=1[CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]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>[F:16][C:17]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:18]=1[CH2:19][C:20]1([OH:26])[CH2:25][CH2:24][N:23]([C:8]([C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[C:5]2[O:1][CH:2]=[N:3][CH:4]=2)=[O:10])[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 533937912-(5-Oxazolyl)benzoic AcidHCID 866808664-(2,4-Difluorobenzyl)-4-hydroxypiperidine hydrochloride

Product 1

HCID 86680870(4-(2,4-Difluorobenzyl)-4-hydroxypiperidin-1-yl)(2-(1,3-oxazol-5-yl)phenyl)methanoneYield 107.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-(1,3-oxazol-5-yl)benzoic acid (0.15 g), 4-(2,4-difluorobenzyl)-4-hydroxypiperidine hydrochloride (0.16 g), HATU (0.36 g) and triethylamine (1.1 mL) in DMF (5.0 mL) was stirred overnight at room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.26 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and 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)

Sources & evidence

ORD record
ord-ff1a2f11adbb45ad8606e9e006747f0e
Source dataset
uspto-grants-2015_11
Patent number
US09193709B2

Reaction notes

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