Hydrochloric Acid → 1-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 469709Notes

Reaction equation

HRID 469709 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[Cl:19][C:20]1[C:21](F)=[N:22][CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1.C(N(CC)CC)C>C(O)C>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:21]2[C:20]([Cl:19])=[CH:25][C:24]([C:26]([F:29])([F:27])[F:28])=[CH:23][N:22]=2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridineHCID 67455816HCID 67455816, compound

Product 1

HCID 674583461-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
175 °C

Procedure

A microwave reaction vessel is charged with (S)-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride, 3-chloro-2-fluoro-5-trifluoromethylpyridine, triethylamine and ethanol. The mixture is heated in a microwave reactor at 175° C. for 1 h, maintaining the watts at 60 to keep the reactor from shutting down. The reaction is cooled to room temperature and concentrated in vacuo to afford an oil which is purified by reverse phase preparative HPLC. Product fractions are combined and concentrated in vacuo to afford title compound (64.4 mg). ESI m/z 417 [M+H]+.

Workup

  1. customA microwave reaction vessel
  2. temperaturemaintaining the watts at 60
  3. temperatureThe reaction is cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. customto afford an oil which
  6. customis purified by reverse phase preparative HPLC
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7db17c660c714c0eab8397d3ea7c2c51
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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