HCID 22050728, compound → HCID 22051076, compound

HRID 1867027Notes

Reaction equation

HRID 1867027 reaction equation
C([NH:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)C1C=CC=CC=1>C(O)(=O)C>[NH2:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1

Participants

3

Reactant 1

HCID 22050728HCID 22050728, compound

Product 1

HCID 22051076HCID 22051076, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a Fischer-Porter bottle, added a solution of 4-(benzylamino)-1-(3-fluorobenzyl)pyridin-2(1H)-one (2.5 g, 8.11 mmol) in glacial acetic acid (20 mL). After the solution was flushed with nitrogen, catalyst was added (10% Pd/C, 2.0 g). The vessel was sealed, evacuated, and purged with hydrogen gas. The system was charged with hydrogen gas (50 psi) and the mixture stirred at room temperature for 4 hours. The system was evacuated and flushed with nitrogen. The reaction mixture was filtered through a bed of celite and washed with fresh ethanol. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate 3:4 v/v). The filtrate was concentrated. 1H-NMR (CD3OD, 400 MHz) δ 7.32 (q, 1H), 7.02 (m, 3H), 5.93 (dd, 1H, J=2.4 Hz, 2.8 Hz), 5.58 (d, 1H, J=2.4 Hz); ES-HRMS m/z 219.0966 (M+H calculated for C12H12N2OF requires 219.0928).

Workup

  1. customAfter the solution was flushed with nitrogen, catalyst
  2. additionwas added (10% Pd/C, 2.0 g)
  3. customThe vessel was sealed
  4. customevacuated
  5. custompurged with hydrogen gas
  6. additionThe system was charged with hydrogen gas (50 psi)
  7. customThe system was evacuated
  8. customflushed with nitrogen
  9. filtrationThe reaction mixture was filtered through a bed of celite
  10. washwashed with fresh ethanol
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customthe residue was purified by flash column chromatography (hexane/ethyl acetate 3:4 v/v)
  13. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-42cbd276b02a4a7faac3647da6c45928
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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