Sodium Hydroxide → 6-[3-[4-chloro-3-[[(methoxycarbonyl)amino]methyl]phenyl]-1H-pyrazol-1-yl]-2H-1-benzopyran-3-carboxylic acid

HRID 1408431Notes

Reaction equation

HRID 1408431 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]4[O:21][CH2:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][C:17]=4[CH:26]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:27][NH:28][C:29]([O:31][CH3:32])=[O:30].[OH-].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]4[O:21][CH2:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][C:17]=4[CH:26]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:27][NH:28][C:29]([O:31][CH3:32])=[O:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67151153methyl 6-[3-[4-chloro-3-[[(methoxycarbonyl)amino]-methyl]phenyl]-1H-pyrazol-1-yl]-2H-1-benzopyran-3-carboxylate2×

Product 1

HCID 671512066-[3-[4-chloro-3-[[(methoxycarbonyl)amino]methyl]phenyl]-1H-pyrazol-1-yl]-2H-1-benzopyran-3-carboxylic acidYield 73%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl 6-[3-[4-chloro-3-[[(methoxycarbonyl)amino]methyl]phenyl]-1H-pyrazol-1-yl]-2H-1-benzopyran-3-carboxylate (i.e. the product of Step C) (100 mg, 0.22 mmol) in 1:1 tetrahydrofuran/water was added NaOH (35 mg 0.85 mmol) and the reaction mixture was stirred at ambient temperature for 6 hrs. After TLC analysis (50% ethyl acetate/pet ether) showed completion of reaction, the organic solvent was concentrated. The resultant aqueous solution was cooled to 0° C., acidified with 1N HCl and extracted three times with ethyl acetate. The combined the organic phases were washed with water, brine, dried over Na2SO4. The solvent was concentrated under vacuum to give compound number 24, a compound of the present invention, (70 mg, 73% yield) as solid.

Workup

  1. customcompletion of reaction
  2. concentrationthe organic solvent was concentrated
  3. temperatureThe resultant aqueous solution was cooled to 0° C.
  4. extractionextracted three times with ethyl acetate
  5. washwere washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe solvent was concentrated under vacuum
  8. customto give compound number 24

Sources & evidence

ORD record
ord-ac1e6aced39e4bbbb2541a71b06b6aea
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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