Diisopropylethylamine → HCID 57559933, compound

HRID 602704Notes

Reaction equation

HRID 602704 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].[NH:18]1[CH2:21][CH:20]([C:22]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[CH:29]=2)([OH:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:19]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:18]2[CH2:21][CH:20]([C:22]([C:28]3[CH:29]=[C:30]([F:35])[CH:31]=[C:32]([F:34])[CH:33]=3)([OH:27])[C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:19]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 67065942HCID 67065942, compound

Product 1

HCID 57559933HCID 57559933, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction mixture of 135 mg (0.44 mmol) of 3-[bromo(4-chlorophenyl)methyl]benzonitrile, 105 mg (0.367 mmol) of 1-azetidin-3-yl-1-(3,5-difluorophenyl)-2,2-dimethylpropan-1-ol (3) and 230 uL (1.32 mmol) of N,N-diisopropylethylamine in 6 mL of acetonitrile was refluxed for 3 h. Then it was concentrated and the residue was dissolved in 5 mL of hexane/ether. 1 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=481 (M+1 35Cl) and 483 (M+1 37Cl). Further elution of the column afforded the other racemic diastereomer of the title compound; Mass Spectrum: m/e=481 (M+1 35Cl) and 483 (M+1 37Cl).

Workup

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

Sources & evidence

ORD record
ord-1cffa17df0b24d289f474c513a82441c
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

Loading…