HCID 68459274, compound → HCID 178465232, compound

HRID 2356847Notes

Reaction equation

HRID 2356847 reaction equation
C([N:5]1[C:9]([NH:10][C:11](=[O:27])[CH:12]([NH:14][C:15](=[O:26])[CH:16]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[OH:17])[CH3:13])=[CH:8][C:7]([C:28]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[N:6]1)(C)(C)C>FC(F)(F)C(O)=O>[F:25][C:20]1[CH:19]=[C:18]([CH:16]([OH:17])[C:15]([NH:14][CH:12]([CH3:13])[C:11]([NH:10][C:9]2[NH:5][N:6]=[C:7]([C:28]3([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[CH:8]=2)=[O:27])=[O:26])[CH:23]=[C:22]([F:24])[CH:21]=1

Participants

3

Reactant 1

HCID 68459274HCID 68459274, compound

Product 1

HCID 178465232HCID 178465232, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.04 g (0.1 mmol) of N-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-yl]-2-[2-(3,5-difluorophenyl)-2-hydroxyacetylamino]propionamide in 2.0 mL of neat trifluoroacetic acid was refluxed for 15 min. The reaction mixture was then cooled to rt, quenched with sat. aq. NaHCO3 and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. Purification on silica gel afforded 2-[2-(3,5-difluorophenyl)-2-hydroxyacetylamino]-N-[5-(1-methyl-4 phenylpiperidin-4-yl)-2H-pyrazol-3-yl]propionamide.

Workup

  1. customquenched with sat. aq. NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-58af26b681fc40bb8392ea38f364c199
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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