Trifluoroacetic acid → 4-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

HRID 1689774Notes

Reaction equation

HRID 1689774 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([O:15][CH2:16][C:17]2[C:18]([C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])=[N:19][O:20][C:21]=2[CH:22]2[CH2:24][CH2:23]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:8]1[CH2:14][CH2:13][CH2:12][CH:11]([O:15][CH2:16][C:17]2[C:18]([C:25]3[C:26]([Cl:32])=[CH:27][CH:28]=[CH:29][C:30]=3[Cl:31])=[N:19][O:20][C:21]=2[CH:22]2[CH2:23][CH2:24]2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593693274-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 593693374-((Azepan-4-yloxy)methyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazoleYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepane-1-carboxylic acid tert-butyl ester (2.0 g, 0.00416 mol) in CH2Cl2 (20 ml) is added trifluoroacetic acid (1.42 g, 0.01248 mol) at 0° C. under N2 atmosphere. Stir the mixture for 3 h at room temperature. Concentrate the reaction mixture in vacuo to give crude product. Purify by column chromatography over alumina (neutral) eluting with 8:2 dichloromethane/methanol to give the title compound 1.4 g (88%). ES/MS m/z 381.1 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture in vacuo
  2. customto give crude product
  3. customPurify by column chromatography over alumina (neutral)
  4. washeluting with 8:2 dichloromethane/methanol

Sources & evidence

ORD record
ord-392135104be746cfb46edaacd5f46466
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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