Oxalyl chloride → HCID 58879975, compound

HRID 1361416Notes

Reaction equation

HRID 1361416 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[C:21](=[O:33])[N:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:23]=[CH:24][CH:25]=1>ClCCl.CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH:19][C:20]1[C:21](=[O:33])[N:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[CH:23]=[CH:24][CH:25]=1)=[O:6]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 5211702,4,5-Trifluorobenzoic acidHCID 588799723-amino-1-(4-fluorophenyl)pyridin-2(1H)-one

Product 1

HCID 58879975HCID 58879975, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,4,5-trifluorobenzoic acid (Aldrich, 704 mg, 4.0 mmol) in dichloromethane (20 mL), was added oxalyl chloride (Aldrich, 0.70 mL, 8.0 mmol) dropwise, followed by two drops of DMF. The reaction mixture was stirred at room temperature for 2 h, and concentrated in vacuo. Toluene (20 mL) was added and the reaction mixture was evaporated in vacuo to remove the excess oxalyl chloride. The residue was dissolved in dichloromethane (20 mL). Half of this acid chloride solution was added to a mixture of 3-amino-1-(4-fluorophenyl)pyridin-2(1H)-one (306 mg, 1.5 mmol) in dichloromethane (5 mL) and TEA (0.5 mL, Aldrich) at 0° C. The reaction mixture was stirred at room temperature for 1 h. The precipitate that formed was collected by filtration, and washed with methanol, to afford the desired product (363 mg, 67% yield) as a solid. MS(ESI+) m/z 363.25 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionToluene (20 mL) was added
  3. customthe reaction mixture was evaporated in vacuo
  4. customto remove the excess oxalyl chloride
  5. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  6. stirringThe reaction mixture was stirred at room temperature for 1 h
  7. customThe precipitate that formed
  8. filtrationwas collected by filtration
  9. washwashed with methanol

Sources & evidence

ORD record
ord-35db9a0b0cea4097821b37a45f95a64b
Source dataset
uspto-grants-2011_02
Patent number
US07880004B2

Reaction notes

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