Acetic Acid → HCID 10254932, compound

HRID 2105997Notes

Reaction equation

HRID 2105997 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]([OH:28])([CH2:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[CH:19]=[CH:18]1)[CH2:4][C:5]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)([CH3:7])[CH3:6].ClC(Cl)C.C(O)(=O)C.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[OH:28][C:3]([C:2]([F:30])([F:1])[F:29])([CH2:4][C:5]([CH3:6])([C:8]1[CH:15]=[CH:14][CH:13]=[C:10]([CH2:11][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[CH:9]=1)[CH3:7])[CH2:16][N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[CH:19]=[CH:18]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 8083MorpholineHCID 57809733HCID 57809733, compound

Product 1

HCID 10254932HCID 10254932, compoundYield 51.2%

Procedure

To a solution of 3-[4,4,4-trifluoro-3-hydroxy-1,1-dimethyl-3-(4-oxo-4H-quinolin-1-ylmethyl)butyl]benzaldehyde (0.05 g, 0.12 mmol), dichloroethane (3.0 mL), and acetic acid (0.09 mL, 1.46 mmol) in an ice bath was added morpholine (0.26 μL, 3.00 mmol). The solution was warmed to room temperature and stirred for 0.5 hours. Triacetoxy sodium borohyride (0.06 g. 0.30 mmol) was added and the reaction stirred at room temperature. After 3.0 hours, the solution was partitioned between EtOAc and 3% NH4OH (3 mL). The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and the solvent was evaporated in vacuo. The product was eluted from a flash chromatography column with EtOAc/hexanes, and concentrated in vacuo to afford 1-[2-hydroxy-4-methyl-4-(3-morpholin-4-ylmethylphenyl)-2-trifluoromethylpentyl]-1H-quinolin-4-one as a colorless solid (0.03 g, 45%).

Workup

  1. stirringthe reaction stirred at room temperature
  2. waitAfter 3.0 hours
  3. customthe solution was partitioned between EtOAc and 3% NH4OH (3 mL)
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo
  9. washThe product was eluted from a flash chromatography column with EtOAc/hexanes
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d27647c8f63f4eca8be8aec890b98aea
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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