N,N-Dimethylethylenediamine → HCID 23448026, compound

HRID 1840405Notes

Reaction equation

HRID 1840405 reaction equation
Cl[C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[CH:10][CH:9]=[N:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[CH:10][CH:9]=[N:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 23448016HCID 23448016, compound

Product 1

HCID 23448026HCID 23448026, compound

Procedure

In a similar manner to Example 1-d, the desired product was prepared starting from 6-chloro-3-methoxy-5,11-diaza-benzo[c]fluoren-7-one (Example 14c-1) and N,N-dimethylethylenediamine. The product was obtained as an orange solid. ESI−MS: m/z 349 (MH+); 1H-NMR (CDCl3): δ2.37 (6H, s), 2.67 (2H, t, J=6.5 Hz), 3.79 (2H, dt, J=5.5 Hz, 6.5 Hz), 3.96 (3H, s), 6.96 (1H, dd, J=9 Hz, 2.5 Hz), 7.04 (1H, d, J=2.5 Hz), 7.25 (1H, brt, J=ca 5.5 Hz), 7.28 (1H, dd, J=4.5 Hz, 7.5 Hz), 7.85 (1H, dd, J=7.5 Hz, 1.5 Hz), 8.67 (1H, dd, 4.5 Hz, 1.5 Hz), 8.96 (1H, d, J=9 Hz).

Workup

  1. customThe product was obtained as an orange solid

Sources & evidence

ORD record
ord-4104a88da6574197acc0404cd63465a9
Source dataset
uspto-grants-2004_01
Patent number
US06680326B2

Reaction notes

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