Trifluoroacetic acid → HCID 86680218, compound

HRID 1428747Notes

Reaction equation

HRID 1428747 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([CH:17]([CH3:39])[C:18](=[O:38])[NH:19][CH2:20][C:21]2[C:22]([C:31]3[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=3)=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=2)[CH:14]=[CH:13][C:3]=1[CH2:4][NH:5]C(=O)OC(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:5][CH2:4][C:3]1[CH:13]=[CH:14][C:15]([CH:17]([CH3:39])[C:18]([NH:19][CH2:20][C:21]2[C:22]([C:31]3[CH:32]=[C:33]([CH3:37])[CH:34]=[CH:35][CH:36]=3)=[N:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=2)=[O:38])=[CH:16][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86680217HCID 86680217, compound

Product 1

HCID 86680218HCID 86680218, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of tert-butyl 2-chloro-4-(1-oxo-1-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methylamino)propan-2-yl)benzylcarbamate (132 mg, 0.234 mmol) in dichloromethane (4 mL), cooled to 0° C., were added trifluoroacetic acid (2 ml). The resulting reaction mixture was stirred for 1 h at 0° C. and 1 hour 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-chlorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (90 mg) was obtained as 83% 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-28a18680687a427ba6cf2ebe43bd9364
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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