Water → HCID 86279168, compound

HRID 588391Notes

Reaction equation

HRID 588391 reaction equation
Cl.[Cl:2][C:3]1[C:4]([N:9]([C@@H:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[N:20][N:21]([CH3:28])[C:22]=3[C:23]([O:25]CC)=[O:24])=[CH:14][CH:13]=2)=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].O>C1COCC1>[Cl:2][C:3]1[C:4]([N:9]([C@@H:29]2[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]2)[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:19]=[N:20][N:21]([CH3:28])[C:22]=3[C:23]([OH:25])=[O:24])=[CH:16][CH:17]=2)=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 117652988HCID 117652988, compound

Product 1

HCID 86279168HCID 86279168, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

EXAMPLE 6 Ethyl 4-(4-{(3-chloropyridin-2-yl)[(3R)-piperidin-3-yl]carbamoyl}phenyl)-1-methyl-1H-pyrazole-5-carboxylate hydrochloride salt (7.65 g, 15.2 mmol) was slurried in 50 mL THF followed by the addition of aqueous NaOH (1 mol/L, 50 mL, 50 mmol). Another 23 mL of water was added and the reaction stirred at room temperature for 1.5 h. THF solvent was removed in vacuo, then pH of residual aqueous phase was adjusted to pH 7 with 1 M aqueous HCl, resulting in precipitation of solids. The solids were collected via filtration and after drying afforded the hydrochloride salt of the title compound as an off-white solid (6.49 g, 97%).

Workup

  1. customTHF solvent was removed in vacuo
  2. customresulting in precipitation of solids
  3. filtrationThe solids were collected via filtration
  4. customafter drying

Sources & evidence

ORD record
ord-3e1fffb21d374194b71ec9fb898889e8
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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