Methanesulfonyl chloride → HCID 15430571, compound

HRID 1740581Notes

Reaction equation

HRID 1740581 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH2:20][CH:19]3[C:31](=[O:33])[NH2:32])=[O:17])=[C:11]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])[CH:10]=2)[CH2:4][CH2:3]1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:40][S:41]([N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH2:20][CH:19]3[C:31](=[O:33])[NH2:32])=[O:17])=[C:11]([O:34][CH2:35][C:36]([F:37])([F:38])[F:39])[CH:10]=2)[CH2:4][CH2:3]1)(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21837244HCID 21837244, compound

Product 1

HCID 15430571HCID 15430571, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(4-piperidinyloxy)-2-(2,2,2-trifluoroethoxy)phenylacetyl)-2-carbamoyl-4-(2-methylphenyl)piperazine hydrochloride (0.20 g, 0.35 mmol) from Example 1 in CH2Cl2 (20 mL) was added methanesulfonoyl chloride (0.045 g, 0.39 mmol) and DIEA (0.14 mL, 0.80 mmol). The solution was stirred at ambient temperature for 6 h and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with 0.25 M aqueous citric acid (25 mL), H2O (25 mL), and saturated aqueous NaHCO3 (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH. The product-containing fractions were combined and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 :hexane, and evaporation of this solution under reduced pressure gave the title compound as an amorphous solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with 0.25 M aqueous citric acid (25 mL), H2O (25 mL), and saturated aqueous NaHCO3 (25 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by pressurized silica gel column chromatography
  8. customthe solvent was removed under reduced pressure
  9. dissolutionThe residue was dissolved in CH2Cl2
  10. customhexane, and evaporation of this solution under reduced pressure

Sources & evidence

ORD record
ord-4ac0602368cb4909912c9a9ae0c2c045
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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