Triethylamine → HCID 66578113, compound

HRID 1528687Notes

Reaction equation

HRID 1528687 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[C:20]=2[NH2:25])=[CH:15][CH:14]=1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.CCOC(C)=O.O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[O:23][N:22]=[C:21]([CH3:24])[C:20]=2[NH:25][C:1](=[O:10])[CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:17][CH:18]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Product 1

HCID 66578113HCID 66578113, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydrocinnamoyl chloride (0.73 mL, 4.9 mmol) was added to a mixture of 5-(4-bromo-phenyl)-3-methyl-isoxazol-4-ylamine (4.1 mmol), triethylamine (1.14 mL, 8.2 mmol), and a few drops of DMF in CH2Cl2, and the reaction was stirred at room temperature for 2 hours. The mixture was diluted with EtOAc and H2O and the organic layer was separated, washed with brine, and concentrated. The residue was purified by dry-load silica gel chromatography (28-48% EtOAc in hexanes) to give the title compound.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. concentrationconcentrated
  4. customThe residue was purified
  5. dry with materialby dry-load silica gel chromatography (28-48% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2a5091e3b3e84f58bec9cfe72cc3f57d
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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