2-Methylpropylenediamine → HCID 10268741, compound

HRID 1861000Notes

Reaction equation

HRID 1861000 reaction equation
[F:1][C:2]1[C:3](/[C:12](/I)=[CH:13]/[C:14](=O)[C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[NH2:22][CH2:23][C:24]([NH2:27])([CH3:26])[CH3:25].[H-].[Na+]>>[NH2:27][C:24]([CH3:26])([CH3:25])[CH2:23][NH:22][C:12]1[CH:13]=[C:14]([C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[C:6](=[O:11])[NH:7][C:8]3[C:4]=2[C:3]=1[C:2]([F:1])=[CH:10][CH:9]=3

Participants

4

Reactant 3

HCID 131282-MethylpropylenediamineHCID 24758Sodium hydrideHCID 10135347(Z)-5-fluoro-4-[1-iodo-3-oxo-3-(1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one

Product 1

HCID 10268741HCID 10268741, compound

Procedure

To a suspension of (Z)-5-fluoro-4-[1-iodo-3-oxo-3-(1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one (from Example 8 above) (79.2 mg, 0.2 mmol) in 1,2-diamino-2-methylpropane (Aldrich, 3 mL, 28.4 mmol) was added NaH (Aldrich, 90%, 36 mg, 1.4 mmol) in portions at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was heated under reflux for 1 hour. The reaction was quenched by pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic extracts were successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by preparative TLC (silica gel, 5% methanol in ethyl acetate) to afford 5-(2-amino-2-methyl-propylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a brown solid. (Yield 4.4 mg, 6.5%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customThe reaction was quenched
  4. additionby pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (10 mL)
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by preparative TLC (silica gel, 5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-0c982a0860e44fa2be6bca2c6df27a14
Source dataset
uspto-grants-2003_03
Patent number
US06531598B1

Reaction notes

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