Lithium hydroxide, monohydrate → HCID 68052781, compound

HRID 1685136Notes

Reaction equation

HRID 1685136 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][O:8][C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][C:26]4=[O:31])=[CH:21][CH:20]=3)=[N:11][N:12]([CH3:18])[C:13]=2[C:14]([O:16]C)=[O:15])=[CH:5][CH:4]=1.O.[OH-].[Li+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][C:26]4=[O:31])=[CH:21][CH:20]=3)=[N:11][N:12]([CH3:18])[C:13]=2[C:14]([OH:16])=[O:15])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68052780HCID 68052780, compound

Product 1

HCID 68052781HCID 68052781, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazole-5-carboxylate T-21 (440 mg, 1.0 mmol) in methanol (10 mL) was added lithium hydroxide monohydrate (124 mg, 3.0 mmol). The reaction mixture was heated in a microwave reactor at 120° C. for 20 minutes. Solvent was removed under reduced pressure. Ethyl acetate and 0.1 N hydrochloric acid were added. The organic layer was washed with saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to afford the desired 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazole-5-carboxylic acid T-22 (100 mg, 0.23 mmol).

Workup

  1. customSolvent was removed under reduced pressure
  2. additionEthyl acetate and 0.1 N hydrochloric acid were added
  3. washThe organic layer was washed with saturated brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customSolvent was evaporated under reduced pressure
  6. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-068833f2a899487ba863e58dcd4ae470
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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