2-Ethylhexanoyl chloride → HCID 23512710, compound

HRID 746536Notes

Reaction equation

HRID 746536 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.[CH2:20]([CH:22]([CH2:26][CH2:27][CH2:28][CH3:29])[C:23](Cl)=[O:24])[CH3:21]>>[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:23](=[O:24])[CH:22]([CH2:20][CH3:21])[CH2:26][CH2:27][CH2:28][CH3:29])[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 791032-Ethylhexanoyl chlorideHCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 23512710HCID 23512710, compound

Procedure

According to the general method of Example 14, 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine and 2-ethylhexanoyl chloride were combined to provide N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-2-ethylhexanamide as a tan powder, m.p. 163.0-164.0° C. 1H NMR (300 MHz, DMSO-d6) δ 8.19 (s, 1H), 8.03 (d, J=8.1 Hz, 11H), 7.79 (m, 11H), 7.61 (dd, J=8.1, 1.2 Hz 11H), 7.44 (dt, J=7.5, 1.2 Hz, 11H), 7.26 (dt, J=7.5, 1.2 Hz, 11H), 6.63 (s, 2H), 4.61 (t, J=6.9 Hz, 2H), 3.12-3.05 (m, 2H), 1.94-1.82 (m, 3H), 1.49-1.03 (m, 10H), 0.76 (t, J=7.2 Hz, 3H), 0.67 (t, J=7.2 Hz, 3H); MS (EI) m/e 381.2533 (381.2529 calcd for C22H31N5O).

Sources & evidence

ORD record
ord-f62093a7f3ae4c44ab8f89b517218593
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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