Dimethylformamide → HCID 89767747, compound

HRID 591491Notes

Reaction equation

HRID 591491 reaction equation
CC[N:3]=C=NCCCN(C)C.[Cl:12][C:13]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:14]=1[CH2:15][O:16][C:17]1[CH:32]=[CH:31][C:20]2[C:21]([O:27][CH2:28][O:29][CH3:30])=[C:22]([C:24](O)=[O:25])[S:23][C:19]=2[CH:18]=1.CN(C=O)C>O>[Cl:12][C:13]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:14]=1[CH2:15][O:16][C:17]1[CH:32]=[CH:31][C:20]2[C:21]([O:27][CH2:28][O:29][CH3:30])=[C:22]([C:24]([NH2:3])=[O:25])[S:23][C:19]=2[CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 89768204HCID 89768204, compound

Product 1

HCID 89767747HCID 89767747, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of HOBt ammonia complex (387 mg), EDCI (487 mg), 6-((2,4-dichlorobenzyl)oxy)-3-(methoxymethoxy)-1-benzothiophene-2-carboxylic acid (700 mg) and DMF (5 mL) was stirred at room temperature for 15 h. Water was added to the mixture and the mixture was extracted with THF-AcOEt. The organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was washed with IPE and hexane to give the title compound (510 mg).

Workup

  1. extractionthe mixture was extracted with THF-AcOEt
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with IPE and hexane

Sources & evidence

ORD record
ord-441b23690d4a4e4ebf643a93828c34f2
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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