2-Aminopyridine → HCID 21193119, compound

HRID 1068213Notes

Reaction equation

HRID 1068213 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>C(O)C>[C:11]([N:8]1[CH2:9][CH2:10][CH:5]([C:3]2[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]3[CH:2]=2)[CH2:6][CH2:7]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 21192975HCID 21192975, compound

Product 1

HCID 21193119HCID 21193119, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 160 mg of 2-bromo-1-(1-benzoyl-4-piperidyl)-1-ethanone (prepared in analogy with Example 523, Step A) in 6 mL ethanol was added 59 mg of 2-aminopyridine. After refluxing for 18 hours, the solvent was evaporated. The mixture was partitioned between EtOAc and saturated sodium bicarbonate solution. Aqueous layer was extracted with EtOAc (3×). The combined organic phase was washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography with 100% EtOAc followed by 10% MeOH in EtOAc to give 78 mg of a solid: 1H NMR (500 MHz, CDCl3) δ1.80 (d, 2H), 2.16 (d, 2H), 3.17 (m, 3H), 3.87 (br, 1H), 4.85 (br, 1H), 6.76 (t, J=6.8 Hz,1H). 7.15 (m,1H), 7.37(s, 1H), 7.42(m, 5H), 7. 55(d, J=9.1 Hz, 1H), 8.08 (d, J=6.9 Hz,1H).

Workup

  1. temperatureAfter refluxing for 18 hours
  2. customthe solvent was evaporated
  3. customThe mixture was partitioned between EtOAc and saturated sodium bicarbonate solution
  4. extractionAqueous layer was extracted with EtOAc (3×)
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography with 100% EtOAc

Sources & evidence

ORD record
ord-956e233a6d3e4d668f6c5be6c8dc5907
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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