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 1966675Notes

Reaction equation

HRID 1966675 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-f71cf500c2c7485d925433961370a600
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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