1-Pyrrolidineethanamine → 3-Methoxy-4-methyl-6-(2-pyrrolidin-1-yl-ethylamino)-5,10-diaza-benzo[c]fluoren-7-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18]3[C:17]4[CH:16]=[N:15][CH:14]=[CH:13][C:12]=4[C:11](=[O:19])[C:10]=3[C:9](OS(C3C=CC(C)=CC=3)(=O)=O)=[N:8][C:7]=2[C:31]=1[CH3:32].[NH2:33][CH2:34][CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:18]3[C:17]4[CH:16]=[N:15][CH:14]=[CH:13][C:12]=4[C:11](=[O:19])[C:10]=3[C:9]([NH:33][CH2:34][CH2:35][N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)=[N:8][C:7]=2[C:31]=1[CH3:32]Participants
3
Procedure
This compound was prepared from toluene-4-sulfonic acid 3-methoxy-4-methyl-7-oxo-7H-5,10-diaza-benzo[c]fluoren-6-yl ester (Example 18c-1) and 1-(2-aminoethyl)pyrrolidine in a similar manner to Example 18d. The desired product was obtained as a reddish powder. ESI−MS: m/z 389 (MH+); 1H-NMR (CDCl3): δ1.86 (4H, m), 2.50 (3H, s), 2.72 (4H, m), 2.90 (2H, t, J=6.5 Hz), 3.89 (2H, quartet like, J=ca 6.5 Hz), 4.02 (3H, s), 7.12 (1H, d, J=9 Hz), 7.18 (1H, brt, J=ca 5 Hz), 7.54 (1H, dd, J=4.5 Hz, 1 Hz), 8.04 (1H, d, J=9 Hz), 8.80 (1H, d, J=4.5 Hz), 9.27 (1H, brs).
Sources & evidence
- ORD record
- ord-f701c1814e8c4bc7ad38dfb972be7873
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680326B2
Reaction notes
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