Sodium Hydroxide → HCID 22244543, compound

HRID 891126Notes

Reaction equation

HRID 891126 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12]C)=[O:11])=[C:5]([CH3:17])[N:4]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:27]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])=[O:28])=[CH:20][CH:19]=2)[N:3]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=[O:11])=[C:5]([CH3:17])[N:4]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][NH:26][C:27]([NH:29][S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=3)(=[O:32])=[O:31])=[O:28])=[CH:22][CH:23]=2)[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22244699HCID 22244699, compound

Product 1

HCID 22244543HCID 22244543, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-[3,5-dimethyl-1-(4-{2-[({[(4-methylphenyl)sulfonyl]amino}carbonyl)amino]ethyl}phenyl)-1H-pyrazol-4-yl]benzoate (step 5, 1.1 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) was added 2 M NaOH aq. (10 mL), and then the resulting mixture was refluxed for 3 h. After removal of the solvent, the crude product was partitioned between saturated citric acid aq. (40 mL) and dichloromethane (50 mL). The organic layer was dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with dichloromethane/methanol (10:1) to afford 500 mg (87%) of the title compound as white solids: MS (ESI) m/z 533 [M+H]+, 531 [M−H]−, 1H-NMR (CDCl3) δ 8.05 (2H, s), 7.71-7.29 (6H, m), 3.55 (2H, t, J=6.1 Hz), 2.88 (2H, t, J=6.1 Hz), 2.42 (3H, s), 2.34 (3H, s), 2.27 (3H, s).

Workup

  1. temperaturethe resulting mixture was refluxed for 3 h
  2. customAfter removal of the solvent
  3. customthe crude product was partitioned between saturated citric acid aq. (40 mL) and dichloromethane (50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customAfter removal of the solvent
  6. customthe crude product was purified by TLC with dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-2628cb4c677e4631920c904d9b9916df
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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