Sodium → 2-[4-({[4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-yl]amino}sulfonyl)phenyl]-2-methylpropanoic acid

HRID 1368618Notes

Reaction equation

HRID 1368618 reaction equation
[Na].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([O:35][CH2:36][CH:37]4[CH2:39][CH2:38]4)=[N:13][N:14]([CH3:34])[C:15]=3[NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:33])([CH3:32])[C:27]([O:29]CC)=[O:28])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:10][C:5]=2[O:4][CH2:3]1>CO.O.O1CCCC1>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]3[C:12]([O:35][CH2:36][CH:37]4[CH2:39][CH2:38]4)=[N:13][N:14]([CH3:34])[C:15]=3[NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:33])([CH3:32])[C:27]([OH:29])=[O:28])=[CH:22][CH:21]=3)(=[O:18])=[O:19])=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 22282041ethyl 2-{4-[([4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-yl]amino)sulfonyl]phenyl}-2-methylpropanoate

Product 1

HCID 222819132-[4-({[4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-yl]amino}sulfonyl)phenyl]-2-methylpropanoic acidYield 36.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

An aqueous solution of sodium hydroxyde (2N, 1 ml) was slowly added to a solution of ethyl 2-{4-[([4-(1,3-benzodioxol-5-yl)-3-(cyclopropylmethoxy)-1-methyl-1H-pyrazol-5-yl]amino)sulfonyl]phenyl}-2-methylpropanoate (Example 75) (83 mg) in a mixture of methanol:water:tetrahydrofuran (1:1:1) (6 ml) and the reaction was heated to 50 C. for 24 h. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride (8 ml) and extracted with dichloromethane (3×8 ml). The organic fraction was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC eluted with dichloromethane:methanol (9:1) yielding the title compound as a white solid (28.8 mg).

Workup

  1. temperaturethe reaction was heated to 50 C
  2. customThe reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride (8 ml)
  3. extractionextracted with dichloromethane (3×8 ml)
  4. dry with materialThe organic fraction was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative TLC
  7. washeluted with dichloromethane:methanol (9:1)

Sources & evidence

ORD record
ord-3792cc2e31af43949ae71874cb65c9e4
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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