Oxalyl chloride → HCID 22142198, compound

HRID 1825651Notes

Reaction equation

HRID 1825651 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-5a8ffd54a8284e718e1dc416880815e7
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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