Triethylamine → 2,4'-Bipyridin-3-yl(4-(3,4-difluorobenzyl)-4-hydroxypiperidin-1-yl)methanone

HRID 240404Notes

Reaction equation

HRID 240404 reaction equation
Cl.Cl.[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:11])=O)[C:4]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.Cl.[F:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:23][C:24]1([OH:30])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]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>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([N:27]2[CH2:28][CH2:29][C:24]([CH2:23][C:22]3[CH:31]=[CH:32][C:33]([F:34])=[C:20]([F:19])[CH:21]=3)([OH:30])[CH2:25][CH2:26]2)=[O:11])[C:4]=1[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=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 84819756[2,4'-Bipyridine]-3-carboxylic acid dihydrochlorideHCID 866808634-(3,4-Difluorobenzyl)-4-hydroxypiperidine hydrochloride

Product 1

HCID 866808642,4'-Bipyridin-3-yl(4-(3,4-difluorobenzyl)-4-hydroxypiperidin-1-yl)methanoneYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 2,4′-bipyridine-3-carboxylic acid dihydrochloride (0.30 g), 4-(3,4-difluorobenzyl)-4-hydroxypiperidine hydrochloride (0.38 g), HATU (0.63 g) and triethylamine (0.77 mL) in DMF (4.0 mL) was stirred at room temperature for 18 hr. 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 magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (0.32 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 magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-38603ad421ce4a648f7f3c296f416e2c
Source dataset
uspto-grants-2014_02
Patent number
US08648079B2

Reaction notes

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