Boron tribromide → HCID 178448739, 화합물

HRID 30972노트

반응식

HRID 30972 반응식
[CH2:1]([N:5]1[C:10](=[O:11])[C:9]([C:12]2[NH:13][S:14](=[O:25])(=[O:24])[C:15]3[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:8]([OH:26])[C:7]([CH:27]([CH3:29])[CH3:28])=[N:6]1)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]([C:12]2[NH:13][S:14](=[O:25])(=[O:24])[C:15]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[C:8]([OH:26])[C:7]([CH:27]([CH3:28])[CH3:29])=[N:6]1)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 25134Boron tribromide2회HCID 178448740HCID 178448740, 화합물

생성물 1

HCID 178448739HCID 178448739, 화합물수율 78%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Butyl-5-hydroxy-6-isopropyl-4-(7-methoxy-1, 1-dioxo-1,2-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-2H-pyridazin-3-one (5e) (56 mg) was dissolved in 3 mL of methylene chloride. BBr3 (466 μL, 1.0 M in methylene chloride) was added and the mixture was stirred at room temperature for 1.5 hours. LC-MS result showed the incompletion of the reaction. BBr3 (0.5 mL, 1.0 M) was added and the reaction mixture was continued to shake at room temperature overnight. LC-MS confirmed that the reaction was close to completion. The reaction mixture was poured onto ice (10 mL), extracted with CHCl3 (20 mL×3). The organic layer was dried over MgSO4, filtered, concentrated under reduced pressure and further purified by flash chromatography on silica gel to give the desired product (5f) (42.2 mg) in 78.0% yield. 1H NMR (400 MHz, CDCl3): δ 7.46 (d, 1H, J=2.8 Hz), 7.16-7.26 (m, 2 H), 4.20 (t, 2H, J=7.2 Hz), 3.34 (m, J=6.8 Hz, 1H), 1.81 (m, 2H), 1.41 (m, 2H), 1.29 (d, 6H, J=6.8 Hz), 1.00 (t, 3H, J=7.4 Hz); LC-MS (ESI+): m/e=407.1 [M+1]+ (exact MS: 406.13).

후처리

  1. customLC-MS result
  2. customthe incompletion of the reaction
  3. waitto shake at room temperature overnight
  4. customwas close to completion
  5. additionThe reaction mixture was poured onto ice (10 mL)
  6. extractionextracted with CHCl3 (20 mL×3)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customfurther purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-f17c5e88cce94e94a4c4b6a4f94a6f69
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425552B2

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