Acetic Anhydride → N-[2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylamino]-ethyl]-acetamide

HRID 1633781Notes

Reaction equation

HRID 1633781 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:20]2[NH:21][CH:22]=[CH:23][CH:24]=2)[C:9]2[C:10](=[O:19])[NH:11][C:12]3[C:17]=2[C:16]=1[C:15]([F:18])=[CH:14][CH:13]=3.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(CC)CC)C>C(Cl)Cl>[F:18][C:15]1[C:16]2[C:17]3[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:19])[C:9]=3[C:8]([C:20]1[NH:21][CH:22]=[CH:23][CH:24]=1)=[CH:7][C:6]=2[NH:5][CH2:4][CH2:3][NH:2][C:25](=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 101323945-(2-amino-ethyl amino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one hydrochloride salt

Product 1

HCID 10132679N-[2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylamino]-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(2-amino-ethylamino)-6-fluoro-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one hydrochloride salt (from Example 10 above) (35.5 mg, 0.1 mmol) in CH2Cl2 (2 mL) were added acetic anhydride (Fisher Scientific, 10.2 mg, 0.1 mmol) and triethylamine (Aldrich, 20.2 mg, 0.2 mmol) at room temperature. The reaction mixture was stirred for 2 hours at the same temperature and then quenched with a saturated aqueous ammonium chloride solution (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were successively washed with water (5 mL) and brine (5 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate and hexanes, filtered, and dried to give N-[2-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylamino]-ethyl]-acetamide as a brown solid. (Yield 13.5 mg, 38.4%).

Workup

  1. customquenched with a saturated aqueous ammonium chloride solution (5 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic extracts were successively washed with water (5 mL) and brine (5 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was triturated with ethyl acetate and hexanes
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-db645b207b4e4fd1946601cf2553327d
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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