4-Methoxybenzenesulfonyl chloride → HCID 22281942, compound

HRID 1062752Notes

Reaction equation

HRID 1062752 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[CH:18]=[CH:17][C:13]2[O:14][CH2:15][O:16][C:12]=2[CH:11]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:14]1[C:13]2[CH:17]=[CH:18][C:10]([C:3]3[C:4]([O:8][CH3:9])=[N:5][N:6]([CH3:7])[C:2]=3[NH:1][S:27]([C:24]3[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=3)(=[O:29])=[O:28])=[CH:11][C:12]=2[O:16][CH2:15]1

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 222819435-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole

Product 1

HCID 22281942HCID 22281942, compoundYield 5.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 5-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole (Preparation 43) (100 mg) and 4-dimethylaminopyridine (50 mg) in pyridine (4 ml) at room temperature was added 4-methoxybenzenesulfonyl chloride (145 mg), the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue quenched with citric acid (10%, 10 ml) and then extracted with ethyl acetate (2×10 ml). The organic fractions were combined and washed with saturated aqueous sodium chloride solution (50 ml) the organic fraction was then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue (259 mg) was purified by preparative HPLC on a 5μ ODS Phenomenex Magellen™ column with a gradient elution of acetonitrile (5% to 95%) and 0.1M NH4OAc (95% to 5%) to yield the desired product as an amorphous white solid (10 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue quenched with citric acid (10%, 10 ml)
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. washwashed with saturated aqueous sodium chloride solution (50 ml) the organic fraction
  5. dry with materialwas then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue (259 mg) was purified by preparative HPLC on a 5μ ODS Phenomenex Magellen™ column with a gradient elution of acetonitrile (5% to 95%) and 0.1M NH4OAc (95% to 5%)

Sources & evidence

ORD record
ord-92b15a038a3c453cb04f56853f8a75cd
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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