Sodium Hydroxide → HCID 66660016, compound

HRID 383790Notes

Reaction equation

HRID 383790 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][N:13]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([NH:22][C:23]3[NH:27][N:26]=[CH:25][CH:24]=3)[N:16]=2)[CH2:12][C@@H:11]([C:28]([O:30]C)=[O:29])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[NH4+].[Cl-]>CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][N:13]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([NH:22][C:23]3[NH:27][N:26]=[CH:25][CH:24]=3)[N:16]=2)[CH2:12][C@@H:11]([C:28]([OH:30])=[O:29])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66660181HCID 66660181, compound

Product 1

HCID 66660016HCID 66660016, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of methyl cis-5-[(tert-butoxycarbonyl)amino]-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyridin-2-yl]piperidine-3-carboxylate (11.0 mg) in MeOH (5 ml) was added 5 M aqueous solution of NaOH (468.0 μl) at room temperature. After stirring for 4 hours, NH4Cl was added for neutralization and the mixture was concentrated. The residue was suspended into the mixed solvent of CHCl3 and MeOH. The insoluble material was removed by filtration. The filtrate was concentrated and the residue was purified with preparative RP-HPLC. The desired fraction was neutralized by addition of aqueous solution of NH3 and concentrated. And the residue was purified again with preparative RP-HPLC (mobile phase: H2O and acetonitlile, without TFA) to give cis-5-[(tert-butoxycarbonyl)amino]-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyridin-2-yl]piperidine-3-carboxylic acid (1.82 mg) as colorless solid.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe insoluble material was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified with preparative RP-HPLC
  5. additionThe desired fraction was neutralized by addition of aqueous solution of NH3
  6. concentrationconcentrated
  7. customAnd the residue was purified again with preparative RP-HPLC (mobile phase: H2O and acetonitlile, without TFA)

Sources & evidence

ORD record
ord-6a90fe0950994e68bc06077227de4869
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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