Cyclopentylamine → 4-Bromo-5-(4-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide

HRID 1510427Notes

Reaction equation

HRID 1510427 reaction equation
[Br:1][C:2]1[C:3]([C:14]([O:16]CC)=O)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C>[Br:1][C:2]1[C:3]([C:14]([NH:24][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:16])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 67121165Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate

Product 1

HCID 533260944-Bromo-5-(4-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate (213 mg, 0.70 mmol) and cyclopentylamine (0.70 mL, 7.0 mmol) in absolute ethanol (8 mL) was heated to reflux overnight. The volatiles were removed in vacuo and the compound was purified by silica gel chromatography eluting with 2% methanol with dichloromethane to afford the title compound: (0.21 g, 0.57 mmol). MS (ESI) m/z (M+H+): 370.9/368.8.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe volatiles were removed in vacuo
  4. customthe compound was purified by silica gel chromatography
  5. washeluting with 2% methanol with dichloromethane

Sources & evidence

ORD record
ord-1dc88497cf854c18aed5c14a1643c623
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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