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

HRID 746496ノート

反応式

HRID 746496 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f8dac6347cce4c3a847712ab2cf6f540
出典データセット
uspto-grants-2008_07
特許番号
US07393859B2

反応ノート

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