Dimethylformamide → HCID 67959278, compound

HRID 1404964Notes

Reaction equation

HRID 1404964 reaction equation
[Br:1][C:2]1[C:3]([O:11][CH:12]([CH3:16])[C:13](O)=[O:14])=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.Cl.C([N:20]=C=NCCCN(C)C)C.CN(C=O)C>O>[NH2:20][C:13](=[O:14])[CH:12]([CH3:16])[O:11][C:3]1[C:2]([Br:1])=[CH:6][S:5][C:4]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67959293HCID 67959293, compound

Product 1

HCID 67959278HCID 67959278, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-{[4-bromo-2-(methoxycarbonyl)thiophen-3-yl]oxy}propanoic acid (220 mg), 1H-benzotriazol-1-ol 1 ammonium salt (162 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (205 mg) and DMF (4 mL) was stirred at room temperature for 1.5 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from a mixed solvent of Et2O and hexane to give the title compound (195 mg, 89%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of Et2O and hexane

Sources & evidence

ORD record
ord-abefe0d4bcfa4f6491cdf0f8d263c3e3
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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