4-(Chloromethyl)benzoyl chloride → N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-(chloromethyl)benzamide

HRID 746496노트

반응식

HRID 746496 반응식
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=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]=[CH:18]1>ClCCl.N1C=CC=CC=1.C(Cl)(Cl)Cl.CO>[NH2:30][C:21]1[C:20]2[N:19]=[CH:18][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][NH:12][C:7](=[O:8])[C:6]3[CH:10]=[CH:11][C:3]([CH2:2][Cl:1])=[CH:4][CH:5]=3)[C:29]=2[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:22]=1

참가 물질

7

반응물 2

HCID 701364-(Chloromethyl)benzoyl chlorideHCID 154537751-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 23512685N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-(chloromethyl)benzamide

시약·촉매·용매 4

HCID 887Methanol용매HCID 1049Pyridine용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

A solution of 4-(chloromethyl)benzoyl chloride (1.06 g, 5.6 mmol) in dichloromethane was added to a suspension of 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 3.9 mmol) in pyridine (250 mL). After 1 hour HPLC analysis indicated that the reaction was complete. The reaction mixture was concentrated under vacuum. The residue was combined with saturated aqueous sodium bicarbonate. A solid was isolated by filtration then dissolved in chloroform containing a small amount of methanol. The solution was washed with saturated aqueous sodium bicarbonate. The organic layer was concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel eluting with 10% methanol in dichloromethane) to provide N1-[4-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-4-(chloromethyl)benzamide as a solid, m.p. 240-300 (dec.). 1H NMR (500 MHz, DMSO-d6) δ 8.49 (t, J=6.0 Hz, 1H), 8.21 (s, 1H), 8.03 (d, J=8.0 Hz, 1H);7.76 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.0 Hz, 1H), 7.46 (d, J=8.0 Hz, 2H), 7.42 (t, J=8.0 Hz, 1H), 7.20 (t, J=8.0 Hz, 1H), 6.80 (broad s, 2H), 4.78 (s, 2H), 4.62 (t, J=7.0 Hz, 2H), 3.28 (q, J=6.0 Hz, 2H), 1.89 (quintet, J=7.0 Hz, 2H), 1.56 (quintet, J=7.0 Hz, 2H); MS (CI) m/e 408 (M+H).

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customA solid was isolated by filtration
  3. washThe solution was washed with saturated aqueous sodium bicarbonate
  4. concentrationThe organic layer was concentrated under vacuum
  5. customThe resulting residue was purified by column chromatography (silica gel eluting with 10% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-f8dac6347cce4c3a847712ab2cf6f540
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393859B2

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