Triethylamine → N-{1-[1-(Benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutyl}-5-chlorothiophene-2-sulfonamide

HRID 748076Notes

Reaction equation

HRID 748076 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][N:16]1[C:20]([CH:21]([NH2:27])[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:19][CH:18]=[N:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:28][C:29]1[S:33][C:32]([S:34](Cl)(=[O:36])=[O:35])=[CH:31][CH:30]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:8]([O:15][N:16]1[C:20]([CH:21]([NH:27][S:34]([C:32]2[S:33][C:29]([Cl:28])=[CH:30][CH:31]=2)(=[O:36])=[O:35])[CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:19][CH:18]=[N:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27339255-Chlorothiophene-2-sulfonyl chlorideHCID 68595201{1-[1-(benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutyl}amine

Product 1

HCID 11419642N-{1-[1-(Benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutyl}-5-chlorothiophene-2-sulfonamideYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a flask containing a mixture of triethylamine (0.045 mL, 0.325 mmol) and {1-[1-(benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutyl}amine (0.081 g, 0.296 mmol) in CH2Cl2 (1 mL) at ambient temperature was added 5-chlorothiophene-2-sulfonyl chloride (0.064 g, 0.296 mmol). After 16 h the mixture was diluted with CH2Cl2 (10 mL) and poured into saturated aqueous NaHCO3 (10 mL). The organic phase was separated and washed sequentially with 1N HCl solution, distilled water, brine and then dried over MgSO4, filtered, and concentrated to an oil. Purification by flash chromatography (hexane/EtOAc, 4:1) afforded the product as a solid (0.084 g, 62%). Mass Spectrum (+ESI): 454 (M+H)+.

Workup

  1. additionIn a flask containing
  2. customThe organic phase was separated
  3. washwashed sequentially with 1N HCl solution
  4. distillationdistilled water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. customPurification by flash chromatography (hexane/EtOAc, 4:1)

Sources & evidence

ORD record
ord-d5f850c6aa5d455998ae40a92d474861
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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