HCID 178450665, compound → HCID 178433633, compound

HRID 2271106Notes

Reaction equation

HRID 2271106 reaction equation
C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:14]3[C:15]([C:20](=[O:30])[N:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[N:22]=3)=[CH:16][NH:17][C:18]=2[CH3:19])[CH:8]=1)CCC>[OH-].[Na+]>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([N:21]2[C:20](=[O:30])[C:15]3=[CH:16][NH:17][C:18]([CH3:19])=[C:13]([C:9]4[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=4)[C:6]([OH:31])=[O:5])[C:14]3=[N:22]2)=[CH:24][CH:25]=1

Participants

3

Reactant 1

HCID 178450665HCID 178450665, compound

Product 1

HCID 178433633HCID 178433633, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3-[2-(4-chlorophenyl)-3,5-dihydro-6-methyl-3-oxo-2H-pyrazolo[4,3-c]pyridin-7-yl]benzoic acid butyl ester (from Example 25, Step a) (0.350 g, 0.803 mmol) in 1M aqueous NaOH (3.9 ml) was stirred at room temperature overnight. The mixture was then filtered from a little dark orange solid, which was washed with water, and the combined filtrates were neutralised to pH 5 by the addition of 5M aqueous HCl. The resulting yellow solid was collected by filtration, washed with water, then hexane, and dried at 70° C. under vacuum to afford 0.223 g (73%) of the title compound; 1H NMR (250 MHz, DMSO-d6) δ2.25 (3H, s), 7.43 (2H, d, J 9.0 Hz), 7.65 (1H, t, J 7.7 Hz), 7.77 (1H, dt, J 7.8, J′1.5 Hz), 8.01 (1H, dt, J 7.7, J′1.4 Hz), 8.07 (1H, t, J 1.4 Hz), 8.12 (2H, d, J 9.0 Hz), 8.60 (1H, d), 12.57 (1H, d, J 6.3 Hz), 13.09 (1H, br s); MS (ES+) m/z 380/382 [MH]+.

Workup

  1. filtrationThe mixture was then filtered from a little dark orange solid, which
  2. washwas washed with water
  3. additionthe combined filtrates were neutralised to pH 5 by the addition of 5M aqueous HCl
  4. filtrationThe resulting yellow solid was collected by filtration
  5. washwashed with water
  6. dry with materialhexane, and dried at 70° C. under vacuum

Sources & evidence

ORD record
ord-a394083ad58f4354ba36e05a5085408b
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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