Dichloromethane → N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl) butyl]phenylmethanesulfonamide

HRID 2270058Notes

Reaction equation

HRID 2270058 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:29]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[C:21]([NH2:30])[C:20]=2[N:19]=[C:18]1[CH2:31][CH2:32][CH2:33][CH3:34].ClCCl>N1C=CC=CC=1>[NH2:30][C:21]1[C:20]2[N:19]=[C:18]([CH2:31][CH2:32][CH2:33][CH3:34])[N:17]([CH2:16][CH2:15][CH2:14][CH2:13][NH:12][S:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:10])=[O:9])[C:29]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 74740Phenylmethanesulfonyl chlorideHCID 155382261-(4-Aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

Product 1

HCID 9847342N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl) butyl]phenylmethanesulfonamideYield 58.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

α-Toluenesulfonyl chloride (0.5 g in 10 ml dichloromethane, 2.7 mmol) was added dropwise to a stirring solution of 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinoline-4-amine (0.75 g, 2.4 mmol), dichloromethane (115 ml), and pyridine (1 ml). The reaction was maintained at room temperature for 4 hours and then concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 9:1 dichloromethane/methanol, Rf 0.16). The fractions containing product were combined and washed with saturated aqueous bicarbonate. The organic layer was dried (MgSO4), filtered, and concentrated. A final recrystallization from dichloromethane/diethyl ether provided 0.65 g of N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl) butyl]phenylmethanesulfonamide as a white crystalline solid, m.p. 197.0-199.5° C. 1H NMR (300 MHz, DMSO-d6) δ 8.02 (d, J=7.6 Hz, 1H), 7.62 (dd, J=8.3, 1.1 Hz, 1H), 7.42 (dt, J=7.5, 1.1 Hz, 1H), 7.35-7.23 (m, 7H), 7.12 (t, J=5.4 Hz, 1H), 6.46 (broad s, 2H), 4.49 (t, J=7.5 Hz, 2H), 4.29 (s, 2H), 2.91 (m, 4H), 1.83-1.42 (m, 8H), 0.96 (t, J=7.4 Hz, 3H);IR (KBr) 3460, 3293, 3226, 3158, 2955, 2931, 2867, 1632, 1586, 1534, 1482, 1437, 1389, 1331, 1152, 1094, 752, 700 cm−1; MS (EI) m/e 465.2204 (465.2198 calcd for C25H31N5O2S); Anal calcd for C25H31N5O2S: C, 64.49; H, 6.71; N, 15.04. 64.15; H, 6.71; N, 15.00.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography (silica gel, 9:1 dichloromethane/methanol, Rf 0.16)
  3. additionThe fractions containing product
  4. washwashed with saturated aqueous bicarbonate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customA final recrystallization from dichloromethane/diethyl ether

Sources & evidence

ORD record
ord-4cc242c2f8614c49b587643d627bb6c7
Source dataset
uspto-grants-2001_12
Patent number
US06331539B1

Reaction notes

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