Ethyl Acetate → HCID 58914804, compound

HRID 1297496Notes

Reaction equation

HRID 1297496 reaction equation
[C:1]([O-:4])(O)=O.[Na+].[NH2:6][C:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[Cl:19])=[CH:10][NH:9][C:8]=1CCCN1C(=O)C2C=CC=CC=2C1=O.[Br:34][CH2:35][C:36](Cl)=[O:37].CCO[C:42]([CH3:44])=[O:43]>>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:11]1[C:7]([NH:6][C:36](=[O:37])[CH2:35][Br:34])=[CH:8][N:9]([CH2:10][CH2:11][CH2:7][N:6]2[C:42](=[O:43])[C:44]3[CH:14]=[CH:13][CH:12]=[CH:17][C:16]=3[C:1]2=[O:4])[CH:10]=1

Participants

5

Reactant 4

HCID 8857Ethyl Acetate2×HCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 68438551HCID 68438551, compound

Product 1

HCID 58914804HCID 58914804, compoundYield 76%

Procedure

Aqueous NaHCO3 (8 eq) was added to the stirred solution of 2-{3-[3-amino-4-(2,4-dichlorophenyl)pyrrolyl]propyl}benzo[c]azoline-1,3-dione (5) (1 eq) in EtOAc at RT. 2-bromoacetyl chloride (1.5 eq) in minimal EtOAc was added slowly to the vigorously stirred reaction solution. The reaction was monitored by LC/MS and determined to be complete within 30 min. The organic layer was separated and washed with water, brine, dried (Na2SO4), filtered, and concentrated to dryness to give the crude N-{4-(2,4-dichlorophenyl)-1-[3-(1,3-dioxobenzo[c]azolin-2-yl)propyl]pyrrol-3-yl}-2-bromoacetamide (6) as a dark yellow glass in 76% yield (−90% pure, LC/MS m/z 536.2 MH+). The product (6) was stored at −4° C. to avoid decomposition.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e329d1c293d943d3807321465e0247c2
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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