Dimethylformamide → HCID 67667417, compound

HRID 1289976Notes

Reaction equation

HRID 1289976 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:13][CH2:12][CH:11]([C:14](O)=O)[CH:10]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25]([CH:27]=[O:28])C.[C:29](Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH2:1]([O:8][CH:9]1[CH2:29][CH2:13][CH2:12][CH:11]([CH2:14][C:27]([NH:25][CH3:24])=[O:28])[CH:10]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 18922350HCID 18922350, compound

Product 1

HCID 67667417HCID 67667417, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.5 gm of the crude product from Step A in 25 mL of methylene chloride was added a drop of DMF and 0.85 mL of oxalyl chloride. The reaction was stirred for 2 h and then concentrated followed by two portions of methylene chloride. The residue was taken up in 25 ml of THF and treated with 3.1 mL of 40% aqueous methylamine. After 2 h, the reaction was concentrated, poured into water and extracted twice with methylene chloride. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography eluting with 75 to 100% ethyl acetate in hexanes to obtain 1.8 mg of title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. additiontreated with 3.1 mL of 40% aqueous methylamine
  3. waitAfter 2 h
  4. concentrationthe reaction was concentrated
  5. additionpoured into water
  6. extractionextracted twice with methylene chloride
  7. washThe organic layers were washed with a portion of brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe residue was purified by flash chromatography
  11. washeluting with 75 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b11854f8749f45318bb21220e59981a2
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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