4-Aminopyridine → HCID 9820865, compound

HRID 2105507Notes

Reaction equation

HRID 2105507 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[NH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>CCOCC.C1COCC1>[N:28]1[CH:29]=[CH:30][C:25]([NH:24][C:18](=[O:22])[C:19]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=3)[CH:8]=2)=[O:20])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 9671271-(4-Fluorobenzyl)-1H-indole

Product 1

HCID 9820865HCID 9820865, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of 4.75 g (21.1 mmol) of 1-(4-fluoro-benzyl)indol in 25 ml of ether is added dropwise at 0° C. and under N2 to a solution of 2.25 ml of oxalyl chloride in 25 ml of ether. The mixture is heated to reflux for 2 hours and the solvent is then evaporated. 50 ml of tetrahydrofuran were then added to the residue, the solution was cooled to −5° C. and treated dropwise with a solution of 4.66 g (49.5 mmol) of 4-aminopyridine in 200 ml of THF. The mixture is heated to reflux for 3 hours and allowed to stand at room temperature overnight. The 4-aminopyridine hydro-chloride is filtered off with suction, the precipitate is washed with THF, the filtrate is concentrated in vacuo and the residue is recrystallized from ethyl acetate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 2 hours
  3. customthe solvent is then evaporated
  4. addition50 ml of tetrahydrofuran were then added to the residue
  5. temperatureThe mixture is heated
  6. temperatureto reflux for 3 hours
  7. filtrationThe 4-aminopyridine hydro-chloride is filtered off with suction
  8. washthe precipitate is washed with THF
  9. concentrationthe filtrate is concentrated in vacuo
  10. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c8fe5ef6cc744e9baaa14057a3f96c8
Source dataset
uspto-grants-2009_08
Patent number
US07579365B2

Reaction notes

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