HCID 23448012, compound → HCID 10137794, compound

HRID 1840412Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

23 mg. of 11-chloro-6-(2-dimethylamino-ethylamino)-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one (Example 27e) was suspended in N,N-dimethylethylenediamine (2.0 ml) and the mixture was stirred at 60° C. overnight under nitrogen. The solution was diluted with dichloromethane and washed with saturated ammonium chloride aqueous solution and dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel thin layer chromatography developed by dichloromethane-methanol-25% ammonia solution=100:5:1. The desired product was obtained as a dark red powder (17 mg). ESI−MS: m/z 435 (MH+); 1H-NMR (CDCl3): δ2.27 (6H, s), 2.34 (6H, s), 2.60-2.66 (4H, m), 3.60 (2H, q-like, J=6.6 Hz), 3.75 (2H, q-like, J=6.3 Hz), 3.96 (3H, s), 5.76 (1H, brt, J=ca 6 Hz), 6.84 (1H, dd, J=2.6 Hz, 9.6 Hz), 6.92 (1H, d, J=4.6 Hz), 7.04 (1H, d, J=2.6 Hz), 7.36 (1H, brt, J=ca 6 Hz), 8.27 (1H, d, J=4.6 Hz), 8.49 (1H, d, 9.6 Hz).

Workup

washwashed with saturated ammonium chloride aqueous solution
dry with materialdried over anhydrous sodium sulfate
customevaporated to dryness
customThe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record: ord-3c722ecfdab94c32a62dc7162e5299bc
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680326B2

Reaction notes

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