Tetrahydrofuran → trans-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylic acid trifluoroacetate

HRID 383788Notes

Reaction equation

HRID 383788 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:19][C@H:18]([NH:20][C:21]([O:23][C@@H:24]([CH3:29])[C:25]([F:28])([F:27])[F:26])=[O:22])[CH2:17][C@H:16]([C:30]([O:32]C)=[O:31])[CH2:15]2)[N:3]=1.C1C[O:37]CC1.[OH-].[Na+].[NH4+].[Cl-]>CO>[F:26][C:25]([F:28])([F:27])[C:24]([OH:37])=[O:23].[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:19][C@@H:18]([NH:20][C:21]([O:23][C@@H:24]([CH3:29])[C:25]([F:27])([F:28])[F:26])=[O:22])[CH2:17][C@H:16]([C:30]([OH:32])=[O:31])[CH2:15]2)[N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66660365methyl cis-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylate

Product 1

HCID 87094126trans-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylic acid trifluoroacetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of the crude carbamate in the mixed solvent of THF (1 ml) and MeOH (6 ml) was added 1 M aqueous solution of NaOH (1 ml). And the mixture was stirred at room temperature for 4 hours. After the addition of excess amount of NH4Cl, the mixture was concentrated. The residue was purified with preparative RP-HPLC to give trans-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]-5-[({[(2S)-1,1,1-trifluoropropan-2-yl]oxy}carbonyl)amino]piperidine-3-carboxylic acid trifluoroacetate (48.0 mg) as pale orange solid.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe residue was purified with preparative RP-HPLC

Sources & evidence

ORD record
ord-538d15150c67441b847bf2f892f2850a
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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