Dichloromethane → N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-benzenesulfonamide

HRID 583859ノート

反応式

HRID 583859 の反応式
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:28]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:29])[C:19]=2[N:18]=[C:17]1[CH2:30][CH2:31][CH2:32][CH3:33].ClCCl>N1C=CC=CC=1>[NH2:29][C:20]1[C:19]2[N:18]=[C:17]([CH2:30][CH2:31][CH2:32][CH3:33])[N:16]([CH2:15][CH2:14][CH2:13][CH2:12][NH:11][S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[C:28]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 155382261-(4-Aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 9868456N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-benzenesulfonamide収率 78.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Benzenesulfonyl chloride (0.45 ml in 10 ml dichloromethane, 3.5 mmol) was added dropwise to a stirring solution of 1-(4-aminobutyl)-2-butyl-1H-imidazo[4,5-c]quinoline-4-amine (1.0 g, 3.2 mmol), dichloromethane (140 ml), and pyridine (0.8 ml). The reaction was maintained at room temperature for four hours and then concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 9:1 dichloromethane\methanol, Rf 0.28) followed by recrystallization from dichloromethane\diethyl ether to provide 1.14 g of N1-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-1-benzenesulfonamide as a white powder, m.p. 75.5-79.0° C. 1H NMR (500 MHz, DMSO-d6) δ 7.99 (d, J=7.7 Hz, 1H), 7.76 (d, J=7.2, 2H), 7.63-7.53 (m, 5H), 7.42 (m, 1H), 7.25 (m, 1H), 6.43 (broad s, 2H), 4.45 (t, J=7.6 Hz, 2H), 2.87 (t, J=7.7 Hz, 2H), 2.78 (m, 2H), 1.79 (m, 4H), 1.55-1.40 (m, 4H), 0.95 (t, J=7.4 Hz, 3H); MS (EI) m/e 451.2036 (451.2042 calcd for C24H29N5O2S); Anal calcd for C24H29N5O2S: C, 63.83; H, 6.47; N, 15.51. Found: C, 63.89; H, 6.42; N, 15.30.

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography (silica gel, 9:1 dichloromethane\methanol, Rf 0.28)
  3. customfollowed by recrystallization from dichloromethane\diethyl ether

出典と根拠

ORDレコード
ord-7d0149d038764fcda3e440798aa948ea
出典データセット
uspto-grants-2005_08
特許番号
US06924293B2

反応ノート

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