2-Dimethylaminopyridine → HCID 53628689, compound

HRID 1260254Notes

Reaction equation

HRID 1260254 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5]1)[CH2:2][CH3:3].CN(C1C=CC=CN=1)C.[O:25]1[C:29]([C:30]2[S:34][C:33]([S:35](Cl)(=[O:37])=[O:36])=[CH:32][CH:31]=2)=[CH:28][CH:27]=[N:26]1>O1CCCC1>[CH2:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:35]([C:33]3[S:34][C:30]([C:29]4[O:25][N:26]=[CH:27][CH:28]=4)=[CH:31][CH:32]=3)(=[O:36])=[O:37])=[CH:13][CH:14]=2)[CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 27953305-isoxazol-5-ylthiophene-2-sulfonyl chlorideHCID 57470085HCID 57470085, compound

Product 1

HCID 53628689HCID 53628689, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-((S)-1-Propyl-pyrrolidin-3-yl)-phenylamine (100 mg, 0.49 mmol) was dissolved in tetrahydrofuran (5 ml). Subsequently, dimethylaminopyridine (24 mg, 0.20 mmol) and 5-(5-isoxazyl)thiophene-2-sulfonyl chloride (159 mg, 0.64 mmol) were added and the reaction mixture stirred overnight at room temperature. The solvent was evaporated under reduced pressure, the residue treated with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product. The crude product was purified with silica gel chromatography with dichloromethane/methanol (100:0 to 96:4) as eluent, yielding the purified product (67 mg, 33%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue treated with water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customto give the crude product
  7. customThe crude product was purified with silica gel chromatography with dichloromethane/methanol (100:0 to 96:4) as eluent

Sources & evidence

ORD record
ord-0689ac36826d450f95ff285dfeff9b50
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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