4-Cyanobenzoyl chloride → HCID 23512651, compound

HRID 1280507Notes

Reaction equation

HRID 1280507 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.[C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)#[N:21]>>[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:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([C:20]#[N:21])=[CH:23][CH:24]=3)[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 801724-Cyanobenzoyl chlorideHCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 23512651HCID 23512651, compound

Procedure

According to the general method of Example 14, 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine and 4-cyanobenzoyl chloride were combined to provide N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-cyanobenzamide as a white powder, m.p. 222.8-225.3 ° C. 1H NMR (300 MHz, DMSO-d6) δ8.73 (t, J=5.7 Hz, 1H), 8.22 (s, 1H), 8.03 (d, J=8.1 Hz, 1H), 7.93 (s, 4H), 7.61 (dd, J=8.4, 1.2 Hz, 1H), 7.43 (dt, J=7.6, 1.5 Hz, 1H), 7.21 (dt, J=7.6, 1.2 Hz, 1H), 6.61 (s, 2H), 4.64 (t, J=7.2 Hz, 2H), 3.33 (m, 2H), 1.96 (quintet, J=7.2 Hz, 2H), 1.58 (quintet, J=7.2 Hz, 2H); IR (KBr) 3441, 3337, 3136, 2945, 2228, 1641, 1545, 1531, 1481, 1396, 1309, 1257, 857, 755 cm−1; MS (El) m/e 384.1699 (384.1699 calcd for C22H20N6O).

Sources & evidence

ORD record
ord-fc97e9061e544685908a312738de7f95
Source dataset
uspto-grants-2002_09
Patent number
US06451810B1

Reaction notes

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