Sodium Thiosulfate → 3-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile

HRID 1966675ノート

反応式

HRID 1966675 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([NH2:19])[C:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][N:3]=1.[CH:20]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[C:25]#[N:26])=O.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]3[N:14]([C:15]([CH3:16])([CH3:18])[CH3:17])[C:20]([C:22]4[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=4[N:30]4[CH:34]=[N:33][CH:32]=[N:31]4)[C:25]#[N:26])=[N:19][C:10]=3[CH:9]=2)=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 585419723-Formyl-4-1,2,4-triazol-1-yl-benzonitrile

生成物 1

HCID 532376053-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzimidazol-2-yl]-4-1,2,4-triazol-1-yl-benzonitrile収率 27.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine (100 mg, 0.39 mmol) in DMF (5 mL) is added 3-formyl-4-1,2,4-triazol-1-yl-benzonitrile (115 mg, 0.58 mmol) at room temperature. Oxone (239 mg, 0.39 mmol) in H2O (1 mL) is added and the solution is stirred for 3 hours. Saturated sodium thiosulfate solution (5 mL) is added and the mixture is extracted with EtOAc (3×15 mL) and H2O (10 mL). The combined organic layer is dried (MgSO4), filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 eluent to afford the title compound (46 mg, 27%) as a white foam. LCMS (ESMS): m/z 436.72 (M++1)

後処理

  1. extractionthe mixture is extracted with EtOAc (3×15 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2 eluent

出典と根拠

ORDレコード
ord-f71cf500c2c7485d925433961370a600
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

反応ノート

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