Diisopropylethylamine → 3-((4-Chlorophenyl){3-[1-(3,5-difluorophenyl)-2,2-dimethylpropyl]azetidin-1-yl}methyl)benzonitrile

HRID 602709Notes

Reaction equation

HRID 602709 reaction equation
Br[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7].[F:18][C:19]1[CH:20]=[C:21]([CH:26]([CH:31]2[CH2:34][NH:33][CH2:32]2)[C:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=[C:23]([F:25])[CH:24]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH:2]([N:33]2[CH2:34][CH:31]([CH:26]([C:21]3[CH:20]=[C:19]([F:18])[CH:24]=[C:23]([F:25])[CH:22]=3)[C:27]([CH3:30])([CH3:28])[CH3:29])[CH2:32]2)[C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[C:6]#[N:7])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 670553513-[Bromo(4-chlorophenyl)methyl]benzonitrileHCID 670659743-[1-(3,5-Difluorophenyl)-2,2-dimethylpropyl]azetidine

Product 1

HCID 119833703-((4-Chlorophenyl){3-[1-(3,5-difluorophenyl)-2,2-dimethylpropyl]azetidin-1-yl}methyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 263 mg (0.86 mmol) of 3-[bromo(4-chlorophenyl)methyl]benzonitrile, 213 mg (0.574 mmol) of 3-[1-(3,5-difluorophenyl)-2,2-dimethylpropyl]azetidine and 300 uL (1.72 mmol) of N,N-diisopropylethylamine in 6 mL of acetonitrile was heated to reflux for 3 h. Then the solution was concentrated and the residue was dissolved in 5 mL of hexane/ether. 1.5 mL of 1N HCl in ether was added to above solution to make salt. It was filtered and washed with hexane/ether. The residue was neutralized with base and was purified by silica gel chromatography with hexanes/ethyl acetate to afford one racemic diastereomer of the title compound; Mass Spectrum: m/e=465 (M+1 35Cl) and 467 (M+1 37Cl).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. concentrationThen the solution was concentrated
  4. dissolutionthe residue was dissolved in 5 mL of hexane/ether
  5. addition1.5 mL of 1N HCl in ether was added to above solution
  6. filtrationIt was filtered
  7. washwashed with hexane/ether
  8. customwas purified by silica gel chromatography with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-08b6004ebc0746de90cd16723c80012e
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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