Dimethylformamide → HCID 22667910, compound

HRID 1007149Notes

Reaction equation

HRID 1007149 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:9][C:10]1[N:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12](O)=[O:13])[CH3:8].C[N:21](C)C=O>C(Cl)Cl>[CH2:7]([O:9][C:10]1[N:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12]([NH2:21])=[O:13])[CH3:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 226482292-Ethoxy-5-iodopyridine-3-carboxylic acid

Product 1

HCID 22667910HCID 22667910, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (6.60 ml, 75.1 mmol) was added to a solution of 2-ethoxy-5-iodonicotinic acid (prepared according to the procedure in WO0127112, 20.0 g, 68.3 mmol) in DCM (400 ml) and N,N-dimethylformamide (0.1 ml) at 0° C. The solution was warmed to room temperature over 18 h and then concentrated in vacuo. The resultant orange oil was dissolved in THF (200 ml) and cooled to 0° C. NH3 (410 ml of a 0.5 M soln. in dioxane, 205 mmol) was added and the mixture was warmed to room temperature over 4 h. The reaction mixture was concentrated in vacuo and triturated with water (150 ml). The solid was filtered and dried to afford the title compound as a beige solid (18.9 g, 64.9 mmol, 95%); m.p. 176-179° C.

Workup

  1. customprepared
  2. customat 0° C
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resultant orange oil was dissolved in THF (200 ml)
  5. temperaturecooled to 0° C
  6. additionin dioxane, 205 mmol) was added
  7. temperaturethe mixture was warmed to room temperature over 4 h
  8. concentrationThe reaction mixture was concentrated in vacuo
  9. customtriturated with water (150 ml)
  10. filtrationThe solid was filtered
  11. customdried

Sources & evidence

ORD record
ord-7a71156c07234d9cb46403f26c2a559f
Source dataset
uspto-grants-2004_09
Patent number
US06794387B2

Reaction notes

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