Benzenepropanoic acid → HCID 4807174, compound

HRID 517002Notes

Reaction equation

HRID 517002 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([CH2:30]CC(O)=O)[CH:29]=[CH:28][CH:27]=[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][CH2:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:6][CH2:7]1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 107Benzenepropanoic 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 4807174HCID 4807174, compoundYield 83.5%

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, 0.208 g, 0.66 mmol) and 3-phenylpropanoic acid (100 mg, 0.66 mmol) taken in dry DCM (30 mL), DIPEA (430 mg, 3.32 mmol) followed by HATU (504 mg, 1.33 mmol) was added at room temperature and stirred overnight. The mixture was then diluted with DCM 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 (0.225 g, 82.72%) as 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-4b9a34c1947749b19c6ed54ab485ec1d
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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