4-Aminopyridine → HCID 14390375, compound

HRID 2351748Notes

Reaction equation

HRID 2351748 reaction equation
C(Cl)(=O)C(Cl)=[O:3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][C:24]([OH:26])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[NH2:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1>CN(C)C=O>[OH2:3].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([CH2:23][C:24]([NH:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)=[O:26])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 65578Oxalyl chloride2×HCID 143904574-chlorophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 14390375HCID 14390375, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (2.43 g, 0.01914 mole) was added dropwise, slowly, to a stirred and chilled solution of 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (4.0 g, 0.014 mole) in dimethylformamide (60 ml). The reaction mixture was stirred at room temperature for 1.5 hour. An additional portion of oxalyl chloride (0.5 ml, 0.0057 mole) was added. After additional stirring at room temperature for 0.5 hr, a solution of 4-aminopyridine (1.81 g, 0.0192 mole) in dimethylformamide (10 ml) was added and the mixture was stirred at room temperature overnight. The mixture was poured into ice water (400 ml) and the resulting solid was collected by filtration, dissolved in hot isopropyl alcohol, filtered hot, and cooled to room temperature to give a solid. The solid was collected by filtration, rinsed with water, and dried under high vacuum to give 1.0 g of title compound, mp>250° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1.5 hour
  2. stirringAfter additional stirring at room temperature for 0.5 hr
  3. stirringthe mixture was stirred at room temperature overnight
  4. filtrationthe resulting solid was collected by filtration
  5. dissolutiondissolved in hot isopropyl alcohol
  6. filtrationfiltered hot
  7. customto give a solid
  8. filtrationThe solid was collected by filtration
  9. washrinsed with water
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-2e943fc413ad4576bb2a6bfafb7c3dfe
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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