Sodium Hydroxide → HCID 68767726, compound

HRID 1171553Notes

Reaction equation

HRID 1171553 reaction equation
C([O:6][CH2:7][C@@H:8]1[CH2:13][C@H:12]([N:14]([CH:16]([CH3:18])[CH3:17])[CH3:15])[CH2:11][CH2:10][C@@H:9]1[N:19]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:35]([F:38])([F:37])[F:36])[CH:33]=3)[N:28]=[CH:27][N:26]=2)[C:20]1=[O:39])(=O)C(C)C.[OH-].[Na+].[NH4+].[Cl-]>CO>[OH:6][CH2:7][C@@H:8]1[CH2:13][C@H:12]([N:14]([CH:16]([CH3:18])[CH3:17])[CH3:15])[CH2:11][CH2:10][C@@H:9]1[N:19]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:35]([F:37])([F:38])[F:36])[CH:33]=3)[N:28]=[CH:27][N:26]=2)[C:20]1=[O:39]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 68768766HCID 68768766, compound

Product 1

HCID 68767726HCID 68767726, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ((1R,2S,5R)-5-(isopropyl(methyl)amino)-2-(2-oxo-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-1-yl)cyclohexyl)methyl isobutyrate (Example 7a, 4 mg) in MeOH (1 mL) was added 1N-NaOH (0.1 mL), and the mixture was stirred for 9 h at rt. After neutralizing with sat. NH4Cl, it was extracted with EtOAc (2×). The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with elution by 0.8:7.2:92 cNH4OH-MeOH—CH2Cl2 to afford the titled compound 1-((1S,2R,4R)-2-(hydroxymethyl)-4-(isopropyl(methyl)amino)cyclohexyl)-3-(6-(trifluoromethyl)quinazolin-4-ylamino)pyrrolidin-2-one. MS found: (M+H)+=480.2.

Workup

  1. extractionwas extracted with EtOAc (2×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel with elution by 0.8:7.2:92 cNH4OH-MeOH—CH2Cl2

Sources & evidence

ORD record
ord-3049dc63822540d0a0375057e59537b9
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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