Methylamine → HCID 23448019, compound

HRID 1840411Notes

Reaction equation

[CH3:1][NH2:2].Cl[C:4]1[C:5]2[C:6]3[C:7]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:8]=4[N:9]=[C:10]([NH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:11]=3[C:12](=[O:17])[C:13]=2[CH:14]=[CH:15][N:16]=1>ClCCl>[CH3:23][N:21]([CH3:22])[CH2:20][CH2:19][NH:18][C:10]1[C:11]2[C:12](=[O:17])[C:13]3[CH:14]=[CH:15][N:16]=[C:4]([NH:2][CH3:1])[C:5]=3[C:6]=2[C:7]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:8]=2[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methylamine (1 ml, 40% in methanol) in dichloromethane (1 ml) was added 11-chloro-6-(2-dimethylamino-ethylamino)-3-methoxy-5,10-diaza-benzo[c]fluoren-7-one (Example 27e) (5.7 mg) and the mixture was stirred at 50° C. for 2 days in a sealed tube. 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=4:1. The desired product was obtained as a dark red powder (1.8 mg). ESI−MS: m/z 378 (MH+); 1H-NMR (CDCl3): δ2.44 (6H, s), 2.77 (2H, t, J=6.3 Hz), 3.14 (3H, d, J=4.9 Hz), 3.82 (2H, q-like, J=6.3 Hz), 3.96 (3H, s), 4.85 (1H, brq, J=ca 5 Hz), 6.89-6.95 (2H, m), 7.04 (1H, d, J=2.6 Hz), 7.30 (1H, brt, J=ca 6 Hz), 8.34 (1H, d, J=9.2 Hz), 8.41 (1H, d, J=4.3 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-dcb269ef02824c0582411bebdfbe0b87
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680326B2

Reaction notes

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