Sodium Hydroxide → HCID 68767726, compound

HRID 1455418Notes

Reaction equation

HRID 1455418 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-51b73ed002ac4f65b75dfb0634f2a313
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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