4-Phenylbutyric Acid → HCID 57647126, compound

HRID 1714886Notes

Reaction equation

HRID 1714886 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[C:25]1([CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:25]1([CH2:31][CH2:32][CH2:33][C:34]([NH:18][C:15]2[CH:16]=[N:17][C:12]([N:9]3[CH2:8][CH2:7][CH:6]([O:5][C:4]4[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=4[C:2]([F:1])([F:23])[F:24])[CH2:11][CH2:10]3)=[CH:13][CH:14]=2)=[O:35])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 47754-Phenylbutyric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68508869HCID 68508869, compound

Product 1

HCID 57647126HCID 57647126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridin-3-amine (225 mg, 0.7 mmol), 4-phenylbutyric acid (131 mg, 0.8 mmol), HATU (380 mg, 1.5 mmol) and DIPEA (465 μL, 2.7 mmol) in DMF (10 mL) was stirred at room temperature for 4 h. After dilution with water, the mixture was extracted with EtOAc. The EtOAc extract was washed with diluted brine, dried (Na2SO4) and concentrated. CombiFlash chromatography (10 g, 40-70% EtOAc in hexanes in 20 min, 20 mL/min, 15 mL/fraction) gave a light brown gum which solidified on standing. Swishing with hexanes-Et2O (1:1) gave the title compound as a white powder.

Workup

  1. extractionAfter dilution with water, the mixture was extracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed with diluted brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customCombiFlash chromatography (10 g, 40-70% EtOAc in hexanes in 20 min, 20 mL/min, 15 mL/fraction) gave a light brown gum which

Sources & evidence

ORD record
ord-16567aa5a6b24dfc9d74c48be00e1710
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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