Dimethylformamide → HCID 19593051, compound

HRID 613496Notes

Reaction equation

HRID 613496 reaction equation
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[Br:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[CH2:23][C:24](O)=[O:25])=[CH:20][CH:19]=[CH:18][C:17]=2[NH:27][C:28](=[O:37])[C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:36].[NH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1>ClCCl>[Br:12][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[CH2:23][C:24](=[O:25])[NH:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1)=[CH:20][CH:19]=[CH:18][C:17]=2[NH:27][C:28](=[O:37])[C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 195092-PyridinemethanamineHCID 65578Oxalyl chlorideHCID 19592412HCID 19592412, compound

Product 1

HCID 19593051HCID 19593051, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of dimethylformamide (17.4 mg) and dichloromethane was added oxalyl chloride (27.7 mg), and the mixture was stirred for 30 minutes at ambient temperature. To the mixture was added 3-bromo-4-carboxymethyl-8-(2,6-dichlorobenzoylamino)quinoline (90 mg) at 0° C., and the mixture was stirred for 1 hour at the same temperature. To the mixture was added 2-aminomethylpyridine (107 mg) at 0° C., and the mixture was stirred for 30 minutes at ambient temperature. The mixture was partitioned between dichloromethane and saturated ammonium chloride solution. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography and recrystallized from ethanol to give 3-bromo-8-(2,6-dichlorobenzoylamino)-4-[(pyridin-2-ylmethyl)carbamoylmethyl]quinoline (58.0 mg).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. stirringthe mixture was stirred for 30 minutes at ambient temperature
  3. customThe mixture was partitioned between dichloromethane and saturated ammonium chloride solution
  4. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin layer chromatography
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-628e341c57ba478caed1e10d1d5d8620
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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