2,1,3-Benzothiadiazole, 4-chlorosulfonyl- → N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-5-yl]-2,1,3-benzothiadiazole-4-sulfonamide

HRID 1062753Notes

Reaction equation

HRID 1062753 reaction equation
[N:1]1[S:2][N:3]=[C:4]2[C:9]([S:10](Cl)(=[O:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=12.[NH2:14][C:15]1[N:19]([CH3:20])[N:18]=[C:17]([O:21][CH3:22])[C:16]=1[C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[O:27]1[C:26]2[CH:30]=[CH:31][C:23]([C:16]3[C:17]([O:21][CH3:22])=[N:18][N:19]([CH3:20])[C:15]=3[NH:14][S:10]([C:9]3[C:4]4[C:5](=[N:1][S:2][N:3]=4)[CH:6]=[CH:7][CH:8]=3)(=[O:12])=[O:11])=[CH:24][C:25]=2[O:29][CH2:28]1

Participants

5

Reactant 2

HCID 27354592,1,3-Benzothiadiazole, 4-chlorosulfonyl-HCID 222819435-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole

Product 1

HCID 22281921N-[4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazol-5-yl]-2,1,3-benzothiadiazole-4-sulfonamideYield 3.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To a solution of 4-dimethylaminopyridine in anhydrous pyridine at 0° C. under an atmosphere of nitrogen was added 2,1,3-benzothiadiazole-4-sulfonyl chloride (142 mg) in pyridine (1.5 ml). After 10 min the reaction was treated with 5-amino-4-(1,3-benzodioxol-5-yl)-3-methoxy-1-methyl-1H-pyrazole (Preparation 43) (100 mg) and the reaction was allowed to warm to room temperature and stirred for 12 h. The reaction was concentrated under reduced pressure, the residue diluted with brine (100 mg) and extracted with dichloromethane (3×50 ml). The combined organic fractions were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC (eluent of 55% water in acetonitrile to 30% water in acetonitrile over 8 mins, then 30% water in acetonitrile for 13 mins. Phenomenex Magellen™ 150 mm×21.5 mm column, 40° C.) to yield the title compound as an off-white solid (7 mg).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionthe residue diluted with brine (100 mg)
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organic fractions were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by HPLC (eluent of 55% water in acetonitrile to 30% water in acetonitrile over 8 mins
  8. wait30% water in acetonitrile for 13 mins

Sources & evidence

ORD record
ord-8d522401662f482d914ca9392c841077
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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