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

HRID 1795913노트

반응식

HRID 1795913 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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=(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, 15.04Found: C, 64.15; H, 6.71; N, 15.00.

후처리

  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

출처 및 근거

ORD 기록
ord-160b09f440c844218e569303b629252f
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030131B2

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