Dimethylformamide → HCID 68513053, compound

HRID 1256924Notes

Reaction equation

HRID 1256924 reaction equation
[C:1]1(C2C=CC=CC=2)[CH:6]=[CH:5][C:4]([S:7]([NH:10][C:11](=[O:30])[CH:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CN(C=O)C>C(Cl)Cl>[CH:4]1([S:7]([NH:10][C:11](=[O:30])[CH:12]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])(=[O:9])=[O:8])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86645228HCID 86645228, compound

Product 1

HCID 68513053HCID 68513053, compoundYield 141.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the compound (1.37 g) obtained in Example 188 (2) in methylene chloride (50 mL) were added oxalyl chloride (800 μL) and DMF in catalytic amount under ice-cooling, and the mixture was stirred at room temperature for 1.5 hr. After concentration under reduced pressure, methylene chloride (8 mL) was added to the residue. Under ice-cooling, the solution was added dropwise to a mixture of the above-mentioned compound (760 mg) in THF (50 mL) and 4-dimethylaminopyridine (1.71 g). After stirring at room temperature for 17 hr, dilute hydrochloric acid (100 mL) was added, and the mixture was extracted with ethyl acetate (100 mL×2). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel chromatography to give the title compound (1.67 g) as a white solid.

Workup

  1. temperaturecooling
  2. concentrationAfter concentration under reduced pressure, methylene chloride (8 mL)
  3. additionwas added to the residue
  4. temperatureUnder ice-cooling
  5. additionthe solution was added dropwise to a mixture of the above-mentioned compound (760 mg) in THF (50 mL) and 4-dimethylaminopyridine (1.71 g)
  6. stirringAfter stirring at room temperature for 17 hr
  7. additiondilute hydrochloric acid (100 mL) was added
  8. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-984d811863d74d018eb760bcdf1bc48b
Source dataset
uspto-grants-2013_06
Patent number
US08461209B2

Reaction notes

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