Sodium → HCID 9914936, compound

HRID 1368614Notes

Reaction equation

HRID 1368614 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:35][CH2:36][CH2:37][O:38][C:39]4[N:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=4)=[N:12][N:13]([CH3:34])[C:14]=3[N:15](S(C3C=CC=CC=3)(=O)=O)[S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1.[Na]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]([O:35][CH2:36][CH2:37][O:38][C:39]4[N:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=4)=[N:12][N:13]([CH3:34])[C:14]=3[NH:15][S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:18])=[O:17])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 22281968HCID 22281968, compound

Product 1

HCID 9914936HCID 9914936, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-N-(phenylsulfonyl)benzene sulfonamide (Example 47) (60 mg) in methanol (4 ml), at room temperature, was added an aqueous solution of sodium hydroxyde (1M, 510□l). After three hours the reaction was quenched by the addition of an aqueous saturated solution of ammonium chloride (5 ml) and extracted with ethyl acetate (3×5 ml). The combined organic fractions were washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The yellow residue was purified by preparative TLC (silica) eluted with dichloromethane:methanol (95:5) yielding the title compound as a colourless oil (26 mg).

Workup

  1. customAfter three hours the reaction was quenched by the addition of an aqueous saturated solution of ammonium chloride (5 ml)
  2. extractionextracted with ethyl acetate (3×5 ml)
  3. washThe combined organic fractions were washed with brine (10 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe yellow residue was purified by preparative TLC (silica)
  7. washeluted with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-9f59db55c233498b9c4d81372e590b4e
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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