4-Aminopyridine → HCID 62235240, compound

HRID 1878672Notes

Reaction equation

HRID 1878672 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.ClCCl>S(Cl)(Cl)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 208126-Chloropicolinic acid

Product 1

HCID 62235240HCID 62235240, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
25 °C

Procedure

6-Chloropicolinic acid (0.50 g, 3.17 mmol) was dissolved in thionyl chloride (5.0 mL) and stirred at 25° C. for 1 hour. The thionyl chloride was evaporated, and 4-aminopyridine (0.28 g, 2.98 mmol), triethylamine (0.415 mL, 2.98 mmol) and dichloromethane (50 mL) were added. The solution was stirred at 25° C. for 18 hours. The reaction mixture was partitioned between dichloromethane (50 mL) and saturated sodium bicarbonate solution (100 mL). The organic layer was dried (sodium sulfate) and concentrated, and the residue was purified by silica gel flash column chromatography to afford the titled compound: 1H NMR (500 MHz, methanol-D4) δ ppm 7.71 (dd, J=7.9, 0.9 Hz, 1H), 7.91-7.95 (m, 2H), 8.05 (t, J=7.8 Hz, 1), 8.20 (dd, J=7.6, 0.6 Hz, 1H), 8.43-8.52 (m, 2H) MS (ESI) m/z=335 (M+H)+.

Workup

  1. customThe thionyl chloride was evaporated
  2. stirringThe solution was stirred at 25° C. for 18 hours
  3. customThe reaction mixture was partitioned between dichloromethane (50 mL) and saturated sodium bicarbonate solution (100 mL)
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-3ba068f4c404419790d2dece89210e49
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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