Oxalyl chloride → HCID 22262076, compound

HRID 1610230Notes

Reaction equation

HRID 1610230 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=[CH:7]2.C(Cl)(=O)C(Cl)=O.Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]([OH:43])[CH:30]([NH2:42])[CH2:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>O1CCCC1.O.CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]([NH:42][CH:30]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:39])[F:40])=[CH:34][CH:33]=1)[CH:29]([C:26]1[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=1)[OH:43])=[O:14])=[CH:9][CH:8]=[CH:7]2

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 728738-Bromo-1-naphthoic acidHCID 516892Sodium BicarbonateHCID 22261728(1RS,2RS)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride

Product 1

HCID 22262076HCID 22262076, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-bromo-1-naphthalenecarboxylic acid (161 mg, 0.64-mmol) in tetrahydrofuran (5 ml) were added oxalyl chloride (0.11 ml, 1.72 mmol) and N,N-dimethylformamide (0.01 ml), and the mixture was stirred at room temperature for 30 min. The reaction solution was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (5 ml). were added (1RS,2SR)-1-(4-fluorophenyl)-1-hydroxy-3-(4-(trifluoromethyl)phenyl)-2-propylamine hydrochloride (150 mg, 0.43 mmol) and saturated aqueous sodium hydrogen carbonate (5 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (50 ml) and extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1). Recrystallization from ethyl acetate-hexane gave the title compound (67 mg, 29%).

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-1:1)
  8. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0597b4035a6343dc8674a5202d07984b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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