Dimethylformamide → HCID 44251085, compound

HRID 1963996Notes

Reaction equation

HRID 1963996 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][O:11][CH2:12][C:13]([OH:15])=O)=[C:4]([C:17]([O:19]C)=[O:18])[CH:3]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH:32]1([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C(=O)(O)[O-].[Na+]>CC(N(C)C)=O.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[CH2:10][O:11][CH2:12][C:13]([N:38]([CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:15])=[C:4]([CH:3]=1)[C:17]([OH:19])=[O:18]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 74567N-CyclohexylanilineHCID 516892Sodium BicarbonateHCID 510399542-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acid

Product 1

HCID 44251085HCID 44251085, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

1.21 g (4.0 mmol) of (2-([4-chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethoxy)acetic acid obtained in Example 1-(i), 32 mg (0.44 mmol) of DMF, and 0.41 mL (4.8 mmol) of oxalyl chloride were added to 12 mL of THF, and stirring was conducted at 0° C. for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and dried. 0.84 g (4.8 mmol) of N-cyclohexylaniline and 8.4 mL of DMA were added to this residue and stirred at room temperature overnight. After completion of the reaction, an aqueous sodium bicarbonate solution was added, extraction was carried out using ethyl acetate, and washing was conducted with a saturated sodium chloride solution. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography, thereby giving 1.77 g of 5-chloro-2-[((2-[cyclohexyl(phenyl)amino]-2-oxoethoxy)acetyl)amino]benzoic acid.methyl ester (yield: 96%).

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customdried
  4. stirringstirred at room temperature overnight
  5. customAfter completion of the reaction
  6. extractionextraction
  7. washwashing
  8. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resulting crude product was separated
  11. custompurified

Sources & evidence

ORD record
ord-311b15be7f334eddb92ae447e05db1eb
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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