Pyridine → 3-[(Phenylsulfonyl)amino]-n-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide

HRID 2105285Notes

Reaction equation

HRID 2105285 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:11]=1[CH3:23])=[O:8].N1C=CC=CC=1.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl.Cl>[C:30]1([S:36]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[C:12]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[C:11]=2[CH3:23])=[O:8])(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 865967603-amino-N-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide

Product 1

HCID 252531443-[(Phenylsulfonyl)amino]-n-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the carboxamide (0.304 mmol) of step 1 above in dichloromethane (5 mL) in a 25 ml round bottom flask was added pyridine (0.304 mmol) and benzenesulfonyl chloride (0.304 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then diluted with hydrochloric acid (2N) and extracted with dichloromethane (2×15 mL). The combined organic extracts were washed with a saturated aqueous solution of sodium bicarbonate (2×10 mL). The organic layers were then dried with magnesium sulfate, filtered, and concentrated under reduced pressure to yield a brown oil. The oil was further purified by silica gel chromatography using 5% ethyl acetate in hexanes as the mobile phase to yield ′3-[(phenylsulfonyl)amino]-N-(2,4,6-trimethyl-3-pyrrolidin-1-ylphenyl)thiophene-2-carboxamide as a white to yellow solid.

Workup

  1. extractionextracted with dichloromethane (2×15 mL)
  2. washThe combined organic extracts were washed with a saturated aqueous solution of sodium bicarbonate (2×10 mL)
  3. dry with materialThe organic layers were then dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a brown oil
  7. customThe oil was further purified by silica gel chromatography

Sources & evidence

ORD record
ord-ecf71992dd9e429ea1baec01c494340f
Source dataset
uspto-grants-2009_08
Patent number
US07579340B2

Reaction notes

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