Boron tribromide → HCID 44218898, 화합물

HRID 1469369

반응식

HRID 1469369 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 44218898HCID 44218898, 화합물수율 5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ec04271437449cebb90402fd984c786
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006269B2

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