Hydrogen Peroxide → 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzamide

HRID 1966745노트

반응식

HRID 1966745 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:18]#[N:19])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1.[NH4+].[OH-:35].OO>CO.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:33]=[CH:32][C:11]3[N:12]([C:28]([CH3:29])([CH3:30])[CH3:31])[C:13]([C:15]4[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=4[N:23]4[CH:27]=[N:26][CH:25]=[N:24]4)[C:18]([NH2:19])=[O:35])=[N:14][C:10]=3[CH:9]=2)=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 532376053-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile

생성물 1

HCID 585418963-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzamide수율 42%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a round bottom flask is added 3-[5-(2-amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile (Example 7) (200 mg, 0.46 mmol) in MeOH (5 mL), followed by the addition of NH4OH (2 mL) and H2O2 (1 mL) (30% in water). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with EtOAc (20 mL), washed with water (10 mL), brine (5 mL), dried under anhydrous Na2SO4 (500 mg), filtered and concentrated. The residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (89 mg, 42%) as a white solid. LCMS (ESMS): m/z 454.73 (M++1)

후처리

  1. washwashed with water (10 mL), brine (5 mL)
  2. customdried under anhydrous Na2SO4 (500 mg)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent

출처 및 근거

ORD 기록
ord-b5fe16b71efe4168b37d27fb2fadc0e6
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420655B2

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