4-Pyridinecarboxaldehyde → 2-(4-tert-butyl-phenyl)-8-[(pyridin-4-ylmethyl)-amino]-2H-phthalazin-1-one

HRID 133106ノート

反応式

HRID 133106 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)[N:8]=[CH:7]2.[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].S(NN)(C1C=CC(C)=CC=1)(=O)=O>C(Cl)Cl>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([N:9]2[N:8]=[CH:7][C:6]3[C:11](=[C:2]([NH:1][CH2:29][C:26]4[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=4)[CH:3]=[CH:4][CH:5]=3)[C:10]2=[O:12])=[CH:18][CH:17]=1)([CH3:22])([CH3:21])[CH3:20]

参加物

6

反応物 4

HCID 133894-PyridinecarboxaldehydeHCID 15303P-ToluenesulfonylhydrazideHCID 5049666Sodium triacetoxyborohydrideHCID 691606278-amino-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one

生成物 1

HCID 114064872-(4-tert-butyl-phenyl)-8-[(pyridin-4-ylmethyl)-amino]-2H-phthalazin-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of the amine (Step E, 45 mg, 0.15 mmol) and CH2Cl2 (10 mL) was added 4-pyridinecarboxaldehyde (0.04 mL, 0.39 mmol) and NaBH(OAc)3 (95 mg, 0.45 mmol). The reaction was stirred at RT for 7 h then quenched with H2O and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give the crude product as an orange oil. The crude product was dissolved in 10 mL CH2Cl2 and stirred with PS-TsNHNH2 resin to remove un-reacted aldehyde. After 1 h, the mixture was filtered through Celite® and concentrated in vacuo. The residue was purified by silica flash chromatography (20-75% EtOAc:hexane) to give the desired product as a light-yellow crystalline solid. MS m/e 385 (M+H)+. Calc'd for C24H24N4O-384.47.

後処理

  1. customthen quenched with H2O
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product as an orange oil
  7. customto remove
  8. customun-reacted aldehyde
  9. waitAfter 1 h
  10. filtrationthe mixture was filtered through Celite®
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica flash chromatography (20-75% EtOAc:hexane)

出典と根拠

ORDレコード
ord-f5fd2b5e61724521a6e8851896d5c524
出典データセット
uspto-grants-2008_06
特許番号
US07390820B2

反応ノート

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