Boron tribromide → HCID 44218898、化合物

HRID 1469369

反応式

HRID 1469369 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:13][CH:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][O:30]CC5C=CC=CC=5)[CH:22]=4)=[CH:17][N:16]=3)[CH2:11]2)=[O:9])[N:2]=1.B(Br)(Br)Br>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:13][CH:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][OH:30])[CH:22]=4)=[CH:17][N:16]=3)[CH2:11]2)=[O:9])[N:2]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 442188993-{5-[3-(2-Benzyloxy-ethoxy)-phenyl]pyridin-2-yloxy}-azetidine-1-carboxylic acid pyridazin-3-ylamide

生成物 1

HCID 44218898HCID 44218898、化合物収率 5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

3-{5-[3-(2-Benzyloxy-ethoxy)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid pyridazin-3-ylamide (Example 9, 325 mg, 0.65 mmol) was dissolved in anhydrous dichloromethane (10 mL) under a nitrogen atmosphere. The mixture was cooled with an ice water bath and boron tribromide in dichloromethane solution (1M, 0.98 mL, 0.98 mmol) was added drop-wise affording a precipitate. The reaction mixture was stirred at 0° C. for 2 hr. The precipitate was collected by filtration and purified by flash chromatography on silica gel eluting with ethyl acetate, then 5-10% methanol in DCM. Further purification by preparative HPLC at pH4 afforded title compound (13 mg, 5%) as colourless solid.

後処理

  1. temperatureThe mixture was cooled with an ice water bath
  2. customaffording a precipitate
  3. filtrationThe precipitate was collected by filtration
  4. custompurified by flash chromatography on silica gel eluting with ethyl acetate
  5. customFurther purification by preparative HPLC at pH4

出典と根拠

ORDレコード
ord-9ec04271437449cebb90402fd984c786
出典データセット
uspto-grants-2015_04
特許番号
US09006269B2

関連ノート

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