p-Methylphenoxyacetic acid → 2-(4-Methylphenoxy)-1-(4-naphthalen-2-ylsulfonylpiperazin-1-yl)ethanone

HRID 517000

Reaction equation

HRID 517000 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].[C:24]1([CH3:35])[CH:29]=[CH:28][C:27]([O:30]CC(O)=O)=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[S:11]([N:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][O:30][C:27]2[CH:28]=[CH:29][C:24]([CH3:35])=[CH:25][CH:26]=2)[CH2:6][CH2:7]1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 70329p-Methylphenoxyacetic acidHCID 81531DiisopropylethylamineHCID 24058752-Chloro-1-[4-(naphthalene-2-sulfonyl)piperazin-1-yl]ethan-1-one2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 11515272-(4-Methylphenoxy)-1-(4-naphthalen-2-ylsulfonylpiperazin-1-yl)ethanoneYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-chloro-1-(4-(naphthalen-2-ylsulfonyl)piperazin-1-yl)ethanone (compound 4, 0.2 g, 0.64 mmol) and 2-(p-tolyloxy)acetic acid (106 mg, 0.64 mmol) in dry DCM (20 mL), DIPEA (495 mg, 3.86 mmol) followed by HATU (486 mg, 1.27 mmol) was added at room temperature and stirred overnight. The mixture was then diluted with DCM and washed with water (2×10 mL) & brine (2×10 mL). The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography to yield the title compound (0.21 g, 77.5%) as an off-white solid.

Workup

  1. additionwas added at room temperature
  2. washwashed with water (2×10 mL) & brine (2×10 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-31e27bbf07fe4a6c83d2dc5203b23350
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Linked notes

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