Hydrochloric Acid → HCID 117840128, compound

HRID 714870Notes

Reaction equation

HRID 714870 reaction equation
[C:1]([C@@:3]1([CH2:31][CH3:32])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[N:17][N:18]([C:20]([CH3:29])([CH3:28])[C:21]([O:23]C(C)(C)C)=[O:22])[CH:19]=3)[N:9]=2)[C:4]1=[O:30])#[N:2].[ClH:33]>C(OCC)(=O)C>[ClH:33].[C:1]([C@@:3]1([CH2:31][CH3:32])[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[N:17][N:18]([C:20]([CH3:28])([CH3:29])[C:21]([OH:23])=[O:22])[CH:19]=3)[N:9]=2)[C:4]1=[O:30])#[N:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117840899HCID 117840899, compound

Product 1

HCID 117840128HCID 117840128, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl 2-(4-((4-((3R)-3-cyano-3-ethyl-2-oxopyrrolidin-1-yl)pyrimidin-2-yl)amino)-1H-pyrazol-1-yl)-2-methylpropanoate (1.0 g) obtained in Step A of Example 199 in ethyl acetate (10 mL) was added a solution of 4 M hydrogen chloride in ethyl acetate (10 mL), and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, and the residue was recrystallized (ethanol/diisopropyl ether) to give the crude title compound (820 mg). The crude title compound (100 mg) was purified by HPLC (C18, mobile phase: water/acetonitrile (containing 10 mM NH4HCO3)), and the solvent was evaporated under reduced pressure. To a solution of the residue in ethanol (3 mL) was added 1 M hydrochloric acid (0.20 mL), and the mixture was stirred at room temperature for 10 min. The solvent was evaporated under reduced pressure, and the residue was recrystallized (ethanol/diisopropyl ether) to give the title compound (820 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was recrystallized (ethanol/diisopropyl ether)
  3. customto give the crude title compound (820 mg)
  4. customThe crude title compound (100 mg) was purified by HPLC (C18, mobile phase: water/acetonitrile (containing 10 mM NH4HCO3))
  5. customthe solvent was evaporated under reduced pressure
  6. additionTo a solution of the residue in ethanol (3 mL) was added 1 M hydrochloric acid (0.20 mL)
  7. stirringthe mixture was stirred at room temperature for 10 min
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was recrystallized (ethanol/diisopropyl ether)

Sources & evidence

ORD record
ord-afd5e105a721470b9d1980a98a1a44f3
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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