4-Aminopyridine → HCID 54465861, compound

HRID 363046Notes

Reaction equation

HRID 363046 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=2[CH2:18][CH3:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>C(Cl)Cl>[N:30]1[CH:31]=[CH:32][C:27]([NH:26][C:13](=[O:15])[C:12]2[CH:16]=[CH:17][C:9]([O:8][CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:10]([CH2:18][CH3:19])[CH:11]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 65578Oxalyl chlorideHCID 53692545HCID 53692545, compound

Product 1

HCID 54465861HCID 54465861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 23-6 (270 mg, 1.0 mmol) in 3.6 mL of CH2Cl2 was added 0.13 mL (1.5 mmol) of oxalyl chloride. The resulting solution was stirred for 1 h, cooled to 0° C. and treated with 380 mg (4.0 mmol) of 4-aminopyridine. Stirring was continued for 1 h before the heterogeneous mixture was diluted with CH2Cl2 and quenched with sat'd NaHCO3. The organic extract was washed with water, brine and dried over Na2SO4. Evaporation of the solvent and column chromatography (3:1 EtOAc/Hexane) afforded product 23-7.

Workup

  1. stirringStirring
  2. waitwas continued for 1 h before the heterogeneous mixture
  3. customquenched with sat'd NaHCO3
  4. extractionThe organic extract
  5. washwas washed with water, brine
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent and column chromatography (3:1 EtOAc/Hexane)

Sources & evidence

ORD record
ord-73d4afa3a5a843f68d413f71c08da494
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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