Dimethylformamide → HCID 67958927, compound

HRID 1404966Notes

Reaction equation

HRID 1404966 reaction equation
[NH2:1][C:2](=[O:15])[CH:3]([CH3:14])[O:4][C:5]1[C:9]([Br:10])=[CH:8][S:7][C:6]=1[C:11](O)=[O:12].Cl.C(N=C=NCCCN(C)C)C.FC1C=C(C2C3OCCNCC=3SC=2)C=CC=1.CN(C=O)C>O>[Br:10][C:9]1[C:5]2[O:4][CH:3]([CH3:14])[C:2](=[O:15])[NH:1][C:11](=[O:12])[C:6]=2[S:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50925146HCID 50925146, compoundHCID 67959327HCID 67959327, compound

Product 1

HCID 67958927HCID 67958927, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-(2-amino-1-methyl-2-oxoethoxy)-4-bromothiophene-2-carboxylic acid (400 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (521 mg), 1-hydroxybenzotriazole 1 hydrate (417 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 saturated aqueous sodium hydrogen carbonate solution 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 (290 mg, 77%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution 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-2dedf39ccb8c4927b2b30c13070a36e1
Source dataset
uspto-grants-2014_12
Patent number
US08916549B2

Reaction notes

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