Dimethylformamide → HCID 15896094, compound

HRID 432590Notes

Reaction equation

HRID 432590 reaction equation
[C:1]([CH2:4][NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[CH3:29])=[O:7])([OH:3])=[O:2].[CH3:30]N(C=O)C.C(Cl)(=O)C(Cl)=O>ClCCl>[CH3:30][O:2][C:1](=[O:3])[CH2:4][NH:5][C:6]([NH:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([N:16]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:12][C:11]=1[CH3:29])=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 15896092HCID 15896092, compound

Product 1

HCID 15896094HCID 15896094, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the carboxylic acid from Example 6 (0.080 g, 0.20 mmol) under a nitrogen atmosphere in dichloromethane (25 ml) at 0° C. were added DMF (20 μl) and oxalyl chloride (31 mg, 0.24 mmol). The mixture was stirred at 0° C. to room temperature for 2 h and then concentrated in vacuo. The residue was dissolved in methanol (4 ml) and dichloromethane (16 ml) and the mixture stirred at room temperature for 16 h. The mixture was then washed with 1M KHSO4 (3 times), saturated sodium bicarbonate solution (3 times) and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant dichloromethane:methanol 96:4) to give a white solid; yield 0.049 g (60%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methanol (4 ml)
  3. stirringdichloromethane (16 ml) and the mixture stirred at room temperature for 16 h
  4. washThe mixture was then washed with 1M KHSO4 (3 times), saturated sodium bicarbonate solution (3 times) and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant dichloromethane:methanol 96:4)
  8. customto give a white solid

Sources & evidence

ORD record
ord-e8b1637526d042da987923ca0eb60711
Source dataset
uspto-grants-2003_12
Patent number
US06664249B1

Reaction notes

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