1,3-Propanediamine → HCID 10221609, compound

HRID 1633774Notes

Reaction equation

HRID 1633774 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][CH2:24][CH2:25][NH2:26].[H-].[Na+]>>[NH2:22][CH2:23][CH2:24][CH2:25][NH:26][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 4281,3-PropanediamineHCID 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 10221609HCID 10221609, compoundYield 26%

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) (118.8 mg, 0.3 mmol) in 1,3-diaminopropane (Aldrich, 3 mL, 35.6 mmol) was added NaH (Aldrich, 90%, 53 mg, 6.6 mmol) in portions at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was heated to 120° C. for 2.5 hours. The reaction was quenched by pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (3×30 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 to give 5-(3-amino-propylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one (Yield 25.3 mg, 26.0%) as the free base which was further purified by RP-HPLC (C-18, eluted with 1% acetonitrile/0.05% acetic acid in H2O) to afford 5-(3-amino-propylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one acetic acid salt.

Workup

  1. temperaturethe reaction mixture was heated to 120° C. for 2.5 hours
  2. customThe reaction was quenched
  3. additionby pouring the reaction mixture into an ice-cold saturated aqueous ammonium chloride solution (20 mL)
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be98c1f4829e443ead1f6b95cf309da5
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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