Boron tribromide → Vatalanib metabolite M26

HRID 1057726노트

반응식

HRID 1057726 반응식
B(Br)(Br)Br.[Cl:5][C:6]1[CH:29]=[CH:28][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:13][N:12]=2)=[CH:8][C:7]=1[O:30]C>ClCCl>[Cl:5][C:6]1[CH:29]=[CH:28][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:13][N:12]=2)=[CH:8][C:7]=1[OH:30]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 6419393HCID 6419393, 화합물

생성물 1

HCID 22741987Vatalanib metabolite M26

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 2 ml boron tribromide (≈1 M in CH2Cl2) is mixed with a suspension of 0.19 g (0.50 mmol) 1-(4-chloro-3-methoxyanilino)-4-(4-pyridylmethyl)phthalazine (Example 68B) in 4 ml dichloromethane at 0° C. under a nitrogen atmosphere. The resinous mixture is left to stand for 18 h at RT, the dichloromethane phase is then decanted, and the glutinous residue stirred with 10 ml THF and 5 ml sat. NaHCO3 solution. The resulting suspension is filtered, the filter residue washed with THF and discarded. The THF phase is separated and dried (Na2SO4), concentrated by evaporation, chromatographed (SiO2; acetate/CH3OH, 40:1→19:1) and title compound crystallized from acetonitrile/methanol: m.p.: 245-246° C.; HPLC: tRet(Grad5-40)=8.8; FAB MS (M+H)+=363.

후처리

  1. waitThe resinous mixture is left
  2. customthe dichloromethane phase is then decanted
  3. filtrationThe resulting suspension is filtered
  4. washthe filter residue washed with THF
  5. customThe THF phase is separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation
  8. customchromatographed (SiO2; acetate/CH3OH, 40:1→19:1) and title compound
  9. customcrystallized from acetonitrile/methanol

출처 및 근거

ORD 기록
ord-32fe2f2b28b741a7b33e000512ac271f
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514974B2

반응 노트

불러오는 중…