2-Dimethylaminopyridine → HCID 22281888, compound

HRID 1368603Notes

Reaction equation

HRID 1368603 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[N:20]([CH3:21])[NH:19][C:18]([O:23][CH3:24])(O)[C:17]=1[C:25]1[CH:33]=[CH:32][C:28]2[O:29][CH2:30][O:31][C:27]=2[CH:26]=1.CN(C1C=CC=CN=1)C>N1C=CC=CC=1>[O:29]1[C:28]2[CH:32]=[CH:33][C:25]([C:17]3[C:18]([O:23][CH3:24])=[N:19][N:20]([CH3:21])[C:16]=3[NH:15][S:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)(=[O:13])=[O:12])=[CH:26][C:27]=2[O:31][CH2:30]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 22281908HCID 22281908, compound

Product 1

HCID 22281888HCID 22281888, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(tert-butyl)benzenesulfonyl chloride (190 mg) was added at room temperature under an atmosphere of nitrogen to a solution of 5-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-3-ol (Preparation 43) (100 mg) and dimethylaminopyridine (50 mg) in anhydrous pyridine (4 ml). The reaction was stirred overnight. The mixture was concentrated under reduced pressure, then a saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml), and brine (6 ml) were sequentially added. The aqueous phase was extracted with ethyl acetate (2×8 ml) and the combined organic fractions were washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified to yield the title compound (10 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiona saturated solution of ammonium chloride (6 ml), ethyl acetate (6 ml), and brine (6 ml) were sequentially added
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×8 ml)
  4. washthe combined organic fractions were washed with brine (10 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified

Sources & evidence

ORD record
ord-c478f6acfafd4114a7fc151432174909
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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