1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine → HCID 18425589, compound

HRID 746544Notes

Reaction equation

HRID 746544 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[C:10]([NH2:19])[C:9]=2[N:8]=[CH:7]1.[CH3:20][O:21][C:22]1[N:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>>[NH2:19][C:10]1[C:9]2[N:8]=[CH:7][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:24](=[O:25])[C:23]3[CH:27]=[CH:28][C:29]([O:31][CH3:32])=[N:30][C:22]=3[O:21][CH3:20])[C:18]=2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

3

Reactant 2

HCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amineHCID 235126882,6-Dimethoxypyridine-3-carbonyl chloride

Product 1

HCID 18425589HCID 18425589, compound

Procedure

According to the general method of Example 14, 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin4-amine and 2,6-dimethoxynicotinoyl chloride were combined to provide N3-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2,6-dimethoxynicotinamide as an off white powder, m.p. 175.0-177.0° C. 1H NMR (300 MHz, DMSO-d6) δ 8.21 (s, 1H), 8.11-8.02 (m, 3H), 7.62 (d, J=8.2 Hz, 1H), 7.42 (t, J=7.5 Hz, 1H), 7.20 (t, J=7.5 Hz, 1H), 6.58 (broad s, 2H), 6.46 (d, J=8.3 Hz, 1H), 4.63 (t, J=7.0 Hz, 2H), 3.90 (s, 3H), 3.88 (s, 3H), 3.30 (m, 2H), 1.90 (m, 2H), 1.57 (m, 2H); MS (EI) m/e 420.1909 (420.1910 calcd for C22H24N6O3).

Sources & evidence

ORD record
ord-4fa3a06ff32c4d06b2aedafee0fdc074
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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