Ammonia → 3-(5-(methylamino)methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-fluoro-1H-indol-3-yl)pyrrole-2,5-dione

HRID 983999Notes

Reaction equation

HRID 983999 reaction equation
Br[CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([C:13]([C:15]4[C:16](=[O:31])[NH:17][C:18](=[O:30])[C:19]=4[C:20]4[C:28]5[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=5)[NH:22][CH:21]=4)=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2.[NH3:32].O1CCC[CH2:34]1>>[CH3:34][NH:32][CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([C:13]([C:15]4[C:16](=[O:31])[NH:17][C:18](=[O:30])[C:19]=4[C:20]4[C:28]5[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=5)[NH:22][CH:21]=4)=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 8028Tetrahydrofuran2×HCID 225567653-(5-Bromomethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-fluoro-1H-indol-3-yl)pyrrole-2,5-dione

Product 1

HCID 225567503-(5-(methylamino)methyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-fluoro-1H-indol-3-yl)pyrrole-2,5-dione

Conditions

Temperature
50 °C

Procedure

3-(5-bromomethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(6-fluoro-1H-indol-3-yl)pyrrole-2,5-dione (330 mg, 0.69 mmol) was added to a solution of ammonia in tetrahydrofuran (2.0 M, 7 mL) in a pressure flask. The solution was heated at 50° C. for 26 hours. An additional 2.0 mL of ammonia in tetrahydrofuran (2.0 M) were added and the reaction mixture heated for another 18 hours. The reaction mixture was concentrated under reduced pressure and the residue subjected to silica gel chromatography to provide 210 mg of the title compound.

Workup

  1. temperaturethe reaction mixture heated for another 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-513b4f59c7c84871a3178e8018dc3259
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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