Hydrochloric Acid → HCID 86729371, compound

HRID 521209Notes

Reaction equation

HRID 521209 reaction equation
[C:1]([CH2:3][C:4]1([N:17]2[CH:21]=[C:20]([C:22]([O:24]C)=[O:23])[C:19]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:18]2)[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].CO.[OH-].[Na+].Cl>C1COCC1>[C:13]([O:12][C:10]([N:7]1[CH2:6][CH2:5][C:4]([N:17]2[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[C:19]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:18]2)([CH2:3][C:1]#[N:2])[CH2:9][CH2:8]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86729370HCID 86729370, compound

Product 1

HCID 86729371HCID 86729371, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 4-(cyanomethyl)-4-[4-(methoxycarbonyl)-3-(phenylamino)-1H-pyrazol-1-yl]piperidine-1-carboxylate (0.12 g, 0.27 mmol) in THF (1.8 mL) was added MeOH (1 mL), and 1M aqueous NaOH (0.82 mL, 0.82 mmol). The mixture was heated to 50° C. for 2 hours. The mixture was then cooled to ambient temperature and acidified to pH 3-4 with 1N aqueous HCl. The mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-10% MeOH/DCM) to afford the title compound.

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by MPLC on silica gel (
  8. washa gradient elution of 0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-2b1ef4da841e4102a571b910f2ddb7dd
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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