Boron tribromide → Vatalanib metabolite M26

HRID 49908ノート

反応式

HRID 49908 の反応式
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]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 6419393HCID 6419393、化合物

生成物 1

HCID 22741987Vatalanib metabolite M26

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2 ml boron tribromide (≈1M 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.

後処理

  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

出典と根拠

ORDレコード
ord-752133b08fb24a7295af5f5b55e78ce9
出典データセット
uspto-grants-2004_03
特許番号
US06710047B2

反応ノート

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