Triethylamine → N-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-piperazinyl)methyl)-N-(2-methylpropyl)methanesulfonamide

HRID 1972603Notes

Reaction equation

HRID 1972603 reaction equation
Cl.Cl.[CH3:3][CH:4]([CH3:18])[CH2:5][N:6]([CH2:11][C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][NH:13]1)[S:7]([CH3:10])(=[O:9])=[O:8].C(N(CC)CC)C.[N+:26]([C:29]1[S:33][C:32]([S:34](Cl)(=[O:36])=[O:35])=[CH:31][CH:30]=1)([O-:28])=[O:27]>C(Cl)Cl>[N+:26]([C:29]1[S:33][C:32]([S:34]([N:16]2[CH2:15][CH2:14][NH:13][C@@H:12]([CH2:11][N:6]([CH2:5][CH:4]([CH3:18])[CH3:3])[S:7]([CH3:10])(=[O:8])=[O:9])[CH2:17]2)(=[O:36])=[O:35])=[CH:31][CH:30]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 217873475-Nitrothiophene-2-sulfonyl chlorideHCID 66582657N-(2-methylpropyl)-N-((2R)-2-piperazinylmethyl)methanesulfonamide dihydrochloride

Product 1

HCID 66582584N-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-piperazinyl)methyl)-N-(2-methylpropyl)methanesulfonamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 5-mL vial was charged with N-(2-methylpropyl)-N-((2R)-2-piperazinylmethyl)methanesulfonamide dihydrochloride (0.144 g, 0.446 mmol) and CH2Cl2 (2 mL). To this was added triethylamine (0.650 mL, 4.66 mmol) in potions at room temperature followed by drop wise addition of 5-nitrothiophene-2-sulfonyl chloride (0.120 g, 0.525 mmol, Enamine LLC, Monmouth Jct. NJ) in CH2Cl2 (1 mL). The mixture was stirred at room temperature for 15 min and then the reaction mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL). The aqueous phase was extracted with CH2Cl2 (2×20 mL) and the combined organic extracts were washed with saturated aqueous NaCl (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (25 g of silica gel, 0 to 10% (2 M NH3 in MeOH) in CH2Cl2) to afford N-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-piperazinyl)methyl)-N-(2-methylpropyl)methanesulfonamide (0.173 g) as a light-brown foam.

Workup

  1. customthe reaction mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (2×20 mL)
  3. washthe combined organic extracts were washed with saturated aqueous NaCl (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (25 g of silica gel, 0 to 10% (2 M NH3 in MeOH) in CH2Cl2)

Sources & evidence

ORD record
ord-8916095ce7d8497898a1fc6cce667fff
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

Loading…