4-(3-Chlorophenyl)butan-2-one → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-[3-(3-chloro-phenyl)-1-methyl-propyl]-amine

HRID 1529019Notes

Reaction equation

HRID 1529019 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH2:14])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][C:24](=O)[CH3:25])[CH:19]=[CH:20][CH:21]=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH:14][CH:24]([CH3:25])[CH2:23][CH2:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([Cl:15])[CH:17]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 2604324-(3-Chlorophenyl)butan-2-oneHCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Product 1

HCID 66577294[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-yl]-[3-(3-chloro-phenyl)-1-methyl-propyl]-amine

Procedure

Prepared according to the procedure described in Example 24, Step 1, using 5-(4-bromo-phenyl)-3-methyl-isoxazol-4-ylamine and 4-(3-chloro-phenyl)-butan-2-one. After silica gel chromatography the crude material was purified via preparatory chiral HPLC (Chiralcel-AD column, 1% EtOH in hexanes, 36 minutes) to afford two separate enantiomers. The first enantiomer eluted from the column is the title compound.

Workup

  1. customPrepared
  2. customAfter silica gel chromatography the crude material was purified via preparatory chiral HPLC (Chiralcel-AD column, 1% EtOH in hexanes, 36 minutes)
  3. customto afford two
  4. customseparate enantiomers
  5. washThe first enantiomer eluted from the column

Sources & evidence

ORD record
ord-2273c9586f5f48c5940e53fd917b24ae
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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