Trifluoroacetic acid → HCID 58966936, compound

HRID 1948263Notes

Reaction equation

HRID 1948263 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([C:14]3[CH:19]=[CH:18][C:17]([N:20]([CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])C(=O)OC(C)(C)C)=[CH:16][CH:15]=3)=[CH:8]2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][CH2:28][CH2:29][N:30]([CH3:31])[CH3:32])=[CH:16][CH:15]=3)[CH:10]=[CH:11][C:12]2=[O:13])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69441013HCID 69441013, compound

Product 1

HCID 58966936HCID 58966936, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

According to Scheme 19 Step 5: tert-Butyl 4-(1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridin-3-yl)phenyl(2-(dimethylamino)ethyl)carbamate (0.16 mmol, 79.0 mg) was dissolved in dry CH2Cl2 (30 mL). Then TFA (7 mL) was added dropwise and the resulting solution was stirred at room temperature for 3 hours. Then the solvent was evaporated under reduced pressure and the resulting residue thus obtained was resulting suspension was taken up in CH2Cl2, washed with a saturated aqueous NaHCO3 solution. The organic solvent was separated, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge CH2Cl2/MeOH(NH3)sat. 95/5. The product fractions were collected and the solvent was evaporated to yield 1-(4-chlorobenzyl)-5-(4-(2-(dimethylamino)ethylamino)phenyl)pyridin-2(1H)-one (16.4 mg, 26%)

Workup

  1. customThen the solvent was evaporated under reduced pressure
  2. customthe resulting residue thus obtained
  3. customwas resulting suspension
  4. washwashed with a saturated aqueous NaHCO3 solution
  5. customThe organic solvent was separated
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified in a manifold (vac.)
  9. customThe product fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e5115aee85484f7a997dcab7db6fa51b
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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