Trifluoroacetic acid → HCID 86680221, compound

HRID 1428755Notes

Reaction equation

HRID 1428755 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([CH:18]([CH3:40])[C:19](=[O:39])[NH:20][CH2:21][C:22]2[C:23]([C:32]3[CH:33]=[C:34]([CH3:38])[CH:35]=[CH:36][CH:37]=3)=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=2)[CH:15]=[CH:14][C:4]=1[CH2:5][NH:6]C(=O)OC(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:6][CH2:5][C:4]1[CH:14]=[CH:15][C:16]([CH:18]([CH3:40])[C:19]([NH:20][CH2:21][C:22]2[C:23]([C:32]3[CH:33]=[C:34]([CH3:38])[CH:35]=[CH:36][CH:37]=3)=[N:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=2)=[O:39])=[CH:17][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86680220HCID 86680220, compound

Product 1

HCID 86680221HCID 86680221, compoundYield 113.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl 2-methoxy-4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzylcarbamate (161 mg, 0.29 mmol) in dichloromethane (4 mL), cooled to 0° C., were added trifluoroacetic acid (2 mL). The resulting reaction mixture was stirred for 2 h at 0° C. and 2 h at room temperature, then basified to pH 8-9 with aq. NaHCO3. The mixture was filtered using celite pad. The filtrate dissolved in dichloromethane and extracted with NaHCO3. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(4-(Aminomethyl)-3-methoxyphenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (151 mg) was obtained as 99% yield.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe mixture was filtered
  3. dissolutionThe filtrate dissolved in dichloromethane
  4. extractionextracted with NaHCO3
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate removed in vacuo
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-471b2411abe94ffd9b0e29b51626473e
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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