Sodium Hydroxide → HCID 66660145, compound

HRID 383791Notes

Reaction equation

HRID 383791 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[NH:20][N:19]=[CH:18][CH:17]=2)[N:12]=[C:11]([N:21]2[CH2:26][C@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:24][C@H:23]([C:33]([O:35]C)=[O:34])[CH2:22]2)[N:10]=1.[OH-].[Na+]>CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[NH:20][N:19]=[CH:18][CH:17]=2)[N:12]=[C:11]([N:21]2[CH2:26][C@H:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:24][C@H:23]([C:33]([OH:35])=[O:34])[CH2:22]2)[N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66660367HCID 66660367, compound

Product 1

HCID 66660145HCID 66660145, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-phenylpiperidine-3-carboxylate trifluoroacetate (34.9 mg) in MeOH (3 ml) was added 2 M aqueous solution of NaOH (1 ml). And the mixture was stirred at room temperature for 1 hour. The mixture was concentrated followed by addition of TFA for neutralization. The residue was purified with preparative RP-HPLC to give cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-phenylpiperidine-3-carboxylic acid trifluoroacetate (34.9 mg) as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionfollowed by addition of TFA for neutralization
  3. customThe residue was purified with preparative RP-HPLC

Sources & evidence

ORD record
ord-d83632bd254c488fb8855b5aad580950
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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