4-Aminotetrahydropyran → 4-Chloro-5-(4-chlorophenyl)-N-(tetrahydro-2H-pyran-4-yl)isoxazole-3-carboxamide

HRID 1510420Notes

Reaction equation

HRID 1510420 reaction equation
[Cl: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.[NH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C(O)C>[Cl:1][C:2]1[C:3]([C:14]([NH:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]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 4192234-AminotetrahydropyranHCID 67121071HCID 67121071, compound

Product 1

HCID 671211234-Chloro-5-(4-chlorophenyl)-N-(tetrahydro-2H-pyran-4-yl)isoxazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-chloro-5-(4-chlorophenyl)isoxazole-3-carboxylate (20 mg, 0.07 mmol) and 4-aminotetrahydropyran (83 μL, 0.7 mmol) in absolute ethanol (1 mL) was heated to reflux for 36 hours. The volatiles were removed in vacuo and the resulting residue was purified by silica gel chromatography, eluting with dichloromethane, to afford the title compound: (16.8 mg, 0.05 mmol).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 36 hours
  3. customThe volatiles were removed in vacuo
  4. customthe resulting residue was purified by silica gel chromatography
  5. washeluting with dichloromethane

Sources & evidence

ORD record
ord-3c7cd71b85554cfda314619be61f5f98
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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