Acetyl chloride → HCID 21999034, compound

HRID 1976738Notes

Reaction equation

HRID 1976738 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:11])[CH:9]=2)[C:4]([C:12]2[C:13](=[O:29])[NH:14][C:15](=[O:28])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][C:22]([NH2:26])=[CH:23][CH:24]=3)[N:19]([CH3:27])[CH:18]=2)=[CH:3]1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38].[O:41]1CC[CH2:43][CH2:42]1>>[C:37]([NH:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([C:16]3[C:15](=[O:28])[NH:14][C:13](=[O:29])[C:12]=3[C:4]3[C:5]4[C:10](=[CH:9][C:8]([NH:11][C:42](=[O:41])[CH3:43])=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[CH:18][N:19]2[CH3:27])=[CH:24][CH:23]=1)(=[O:39])[CH3:38]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 21999014HCID 21999014, compound

Product 1

HCID 21999034HCID 21999034, compoundYield 23%

Conditions

Temperature
0 °C

Procedure

3,4-Bis-(1-methyl-6-amino-1H-indol-3-yl)-pyrrole-2,5-dione (50 mg, 0.13 mmole) was dissolved in tetrahydrofuran (2.5 mL) and cooled to 0° C. Triethylamine (38.5 μl, 0.27 mm) was added followed by acetyl chloride (19.4 pl, 0.27 mmole). The reaction was stirred for 30 min, then concentrated. The reaction mixture was dissolved in chloroform, washed with 0.1 N hydrochloric acid and the organic was dried over magnesiun sulfate, filtered and concentrated. The product was purified by column chromatography in 5% methanol/ethyl acetate to give N-{3-[4-(6-acetylamino-1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-1-methyl-1H-indol-6-yl}-acetamide (14 mg, 23%).

Workup

  1. concentrationconcentrated
  2. dissolutionThe reaction mixture was dissolved in chloroform
  3. washwashed with 0.1 N hydrochloric acid
  4. dry with materialthe organic was dried over magnesiun sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by column chromatography in 5% methanol/ethyl acetate

Sources & evidence

ORD record
ord-18530413b6be437b9debee77358d9b72
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

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