Boron tribromide → [2-(4-acetamidophenylsulfanyl)-7-hydroxy-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

HRID 1864591

反応式

HRID 1864591 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[N:21]=[C:20]([NH:22][C:23]3[NH:24][N:25]=[C:26]([CH3:28])[CH:27]=3)[C:19]3[C:14](=[CH:15][C:16]([O:29]C)=[CH:17][CH:18]=3)[N:13]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].B(Br)(Br)Br>ClC(Cl)C.ClCCl>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[N:21]=[C:20]([NH:22][C:23]3[NH:24][N:25]=[C:26]([CH3:28])[CH:27]=3)[C:19]3[C:14](=[CH:15][C:16]([OH:29])=[CH:17][CH:18]=3)[N:13]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

参加物

5

反応物 2

HCID 25134Boron tribromide2 回HCID 178418798HCID 178418798、化合物

生成物 1

HCID 178418855[2-(4-acetamidophenylsulfanyl)-7-hydroxy-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 63651,1-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

A solution of [2-(4-acetamidophenylsulfanyl)-7-methoxy-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (23 mg, 5.54.10−5 mol) in dichloroethane (3 mL) is treated with 1M BBr3 in dichloromethane (222 μL, 2.21.10−4 mol). The mixture of heated at 80° C. for 4 hours before 1M BBr3 in DCM (222 μL, 2.21.10−4 mol) is added. The reaction mixture is heated at 80° C. for a further 3 hours. The solvent is evaporated and methanol is added to the residue to quench residual BBr3. The solvent is evaporated in vacuo and this operation repeated 3 times. 1M HCl (2 mL) is added to the solid residue and the suspension stirred at room temperature for 15 hours. The solid is collected by filtration and suspended in a mixture water/EtOH (3/1, 8 mL). The mixture is neutralized with NaHCO3 and stirred for 2 hours at room temperature. The solid is then collected by filtration, rinsed with water and diethyl ether to give the desired [2-(4-acetamidophenylsulfanyl)-7-hydroxy-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

後処理

  1. additionThe mixture
  2. additionis added
  3. customThe solvent is evaporated
  4. additionmethanol is added to the residue
  5. customto quench residual BBr3
  6. customThe solvent is evaporated in vacuo
  7. addition1M HCl (2 mL) is added to the solid residue
  8. filtrationThe solid is collected by filtration
  9. stirringstirred for 2 hours at room temperature
  10. filtrationThe solid is then collected by filtration
  11. washrinsed with water and diethyl ether

出典と根拠

ORDレコード
ord-ff62038026b646ffa39b093dabe7f7d2
出典データセット
uspto-grants-2009_12
特許番号
US07625913B2

関連ノート

読み込み中…