Dichloromethane → HCID 178459483, compound

HRID 1954741Notes

Reaction equation

HRID 1954741 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:14]([C:15]([OH:17])=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[C:21](Cl)(=O)[C:22](Cl)=O.Cl[CH2:28]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6](=[O:18])[C:7]3[C:14]([C:15]([O:17][CH2:28][CH:21]=[CH2:22])=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 178524941HCID 178524941, compound2×

Product 1

HCID 178459483HCID 178459483, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a solution of 7-chloro-3-(carboxy)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (500 mg, 1.7 mmol) (compound of Example 9) in dichloromethane (15 mL) was added N,N-dimethylformamide (2 drops) and then in one portion oxalyl chloride (300 μL, 3.4 mmol). The resulting solution was stirred for 24 hours at room temperature, concentrated by rotary evaporation, and allyl alcohol (15 mL) was added to the residue. The mixture was heated at 100° C. for 15 minutes and concentrated by rotary evaporation. The residue was purified by flash chromatography eluting with dichloromethane:methanol (95:5) to give the title compound as a solid (358 mg, 63% yield. 247-249° C.).

Workup

  1. concentrationconcentrated by rotary evaporation, and allyl alcohol (15 mL)
  2. additionwas added to the residue
  3. temperatureThe mixture was heated at 100° C. for 15 minutes
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by flash chromatography
  6. washeluting with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-f0abc53cc044445ba212dce47ba92f3b
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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