Oxalyl chloride → HCID 22142198, compound

HRID 2414502Notes

Reaction equation

HRID 2414502 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH:14]=1)[O:11][C:10]([C:22](O)=[O:23])=[CH:9][C:8]2=[O:25])[CH3:3].C(Cl)(=O)C([Cl:29])=O>CN(C=O)C.C(Cl)Cl>[CH2:2]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH:14]=1)[O:11][C:10]([C:22]([Cl:29])=[O:23])=[CH:9][C:8]2=[O:25])[CH3:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 69269800HCID 69269800, compound

Product 1

HCID 22142198HCID 22142198, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round bottom flask equipped with a reflux condenser, nitrogen inlet and magnetic stirrer is placed 250 mg (0.68 mmol, 1.0 equiv.) of 6-Ethoxy-8-(4-methyl-piperazin-1-yl)-4-oxo-4H-chromene-2-carboxylic acid hydrochloride salt (Reference Example 23d) and 20 mL of methylene chloride. To the stirring suspension is then added 129.5 mg, 164 L (1.02 mmol, 1.5 equiv.) of oxalyl chloride followed by addition of one drop of DMF from a 50 microliter syringe to act as catalyst. The mixture is stirred for 2 hours, then concentrated to dryness on a rotary evaporator under a nitrogen atmosphere, followed by drying under high vacuum. The completeness of the reaction was ascertained by analysis of an aliquot, which was quenched with a THF solution of methylamine, by LC/MS. The crude material was used as obtained in the subsequent amidation reaction.

Workup

  1. customInto a 100 mL round bottom flask equipped with a reflux condenser, nitrogen inlet and magnetic stirrer
  2. concentrationconcentrated to dryness on a rotary evaporator under a nitrogen atmosphere
  3. customby drying under high vacuum
  4. customwas quenched with a THF solution of methylamine, by LC/MS
  5. customas obtained in the
  6. customsubsequent amidation reaction

Sources & evidence

ORD record
ord-9a39b0d031364308a07240df7d0d14d8
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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