Acetic Anhydride → HCID 10298109, compound

HRID 427767Notes

Reaction equation

HRID 427767 reaction equation
[OH:1][CH2:2][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[C:13](=[O:31])[NH:14][C:15](=[O:30])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[CH:23][CH:24]=3)[N:19]([CH3:29])[CH:18]=2)=[CH:4]1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>O>[CH3:29][N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)[C:17]([C:16]2[C:15](=[O:30])[NH:14][C:13](=[O:31])[C:12]=2[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:3]([CH2:2][O:1][C:32](=[O:34])[CH3:33])[CH:4]=2)=[CH:18]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9801985HCID 9801985, compound

Product 1

HCID 10298109HCID 10298109, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slurry of 3-(1-hydroxymethyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (120 mg, 0.288 mmol) (prepared as described in U.S. Ser. No. 09/268,887 (Compound II)) in 3 mL of acetic anhydride (Aldrich) was stirred at room temperature for 19 hours, and at 100° C. for 2.5 hours. The resulting solution was cooled, diluted with water, and extracted with EtOAc. The EtOAc layer was washed with water, brine, dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give 77.1 mg of acetic acid 3-[4-(1-methyl-6-nitro-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3yl]-indol-1-ylmethyl ester. (Yield 53%).

Workup

  1. temperatureThe resulting solution was cooled
  2. extractionextracted with EtOAc
  3. washThe EtOAc layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a7d8b6ab3b29466dad040476e4343244
Source dataset
uspto-grants-2001_11
Patent number
US06313143B1

Reaction notes

Loading…