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

HRID 133106

반응식

HRID 133106 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f5fd2b5e61724521a6e8851896d5c524
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07390820B2

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