Dimethylformamide → HCID 44251013, compound

HRID 1963992Notes

Reaction equation

HRID 1963992 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][CH:39]2[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>C1COCC1.O.CC(N(C)C)=O>[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[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)[CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:15])=[C:4]([CH:3]=1)[C:17]([OH:19])=[O:18]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7582DicyclohexylamineHCID 65578Oxalyl chlorideHCID 510399542-(2-((4-Chloro-2-(methoxycarbonyl)phenyl)amino)-2-oxoethoxy)acetic acid

Product 1

HCID 44251013HCID 44251013, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

1.0 g (3.3 mmol) of (2-([4-chloro-2-(methoxycarbonyl)phenyl]amino)-2-oxoethoxy)acetic acid, a catalytic quantity of DMF, and 505 mg (3.98 mmol) of oxalyl chloride were stirred at 0° C. for 1.5 hours in 10 mL of THF. After completion of the reaction, the solvent was distilled off under reduced pressure. 0.66 g (3.6 mmol) of dicyclohexylamine, and 10 mL of DMA were added to this residue, and stirred at room temperature for 2 hours. After completion of the reaction, water was added, and the precipitated crystals were collected by filtration and dried to give the crude product of 5-chloro-2-(([2-(dicyclohexylamino)-2-oxoethoxy]acetyl)amino)benzoic acid.methyl ester. The crude product was then used in the subsequent stage without being purified.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionwas added
  4. filtrationthe precipitated crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-9e1f7542351a44489c8189fd1c30ad6d
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Reaction notes

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