Potassium Iodide → 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride

HRID 9427

反応式

HRID 9427 の反応式
[NH2:1][C:2]([NH2:4])=[S:3].[I-].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][Cl:26])[C:19]([CH2:27][O:28][CH2:29][CH3:30])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1>CN(C=O)C>[ClH:26].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][S:3][C:2](=[NH:4])[NH2:1])[C:19]([CH2:27][O:28][CH2:29][CH3:30])=[N:18][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1

参加物

5

反応物 3

HCID 4875Potassium IodideHCID 2723790ThioureaHCID 219843917-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline

生成物 1

HCID 219844052-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride収率 95.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

Thiourea (0.29 g, 3.8 mmol) and potassium iodide (0.052 g, 3.1 mmol) were sequentially added to a suspension of 7-bromo-1-(5-chloropentyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (1.3 g, 3.2 mmol) in DMF (15 mL), and the reaction was heated at 110° C. for 24 hours. The DMF was removed under reduced pressure, and the residue was partitioned between saturated aqueous sodium bicarbonate (40 mL) and dichloromethane (50 mL). The mixture was adjusted to pH 7 with the addition of 10% hydrochloric acid. Product remained on the walls of the reaction flask and was dissolved with methanol. The resulting solution was concentrated under reduced pressure to provide a solid. The aqueous layer was concentrated under reduced pressure, and the resulting solid was triturated with methanol and isolated by filtration. The filtrate was concentrated under reduced pressure, and the residue was triturated and isolated as described above. The isolated solids were combined and dried under high vacuum to provide 1.49 g of 2-[5-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)pentyl]isothiourea hydrochloride as a yellow solid.

後処理

  1. customThe DMF was removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate (40 mL) and dichloromethane (50 mL)
  3. additionThe mixture was adjusted to pH 7 with the addition of 10% hydrochloric acid
  4. dissolutionwas dissolved with methanol
  5. concentrationThe resulting solution was concentrated under reduced pressure
  6. customto provide a solid
  7. concentrationThe aqueous layer was concentrated under reduced pressure
  8. customthe resulting solid was triturated with methanol
  9. customisolated by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was triturated
  12. customisolated
  13. customdried under high vacuum

出典と根拠

ORDレコード
ord-d3476380362741e8b181f688fb0be9e4
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

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