Sodium Thiosulfate → HCID 53238529, compound

HRID 1966785Notes

Reaction equation

HRID 1966785 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.[CH3:20][N:21]1[C:25]([CH3:26])=[C:24]([C:27]2[CH:28]=[CH:29][C:30]([N:35]3[CH:39]=[N:38][CH:37]=[N:36]3)=[C:31]([CH:34]=2)[CH:32]=O)[CH:23]=[N:22]1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[C:15]([N:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:9][C:10]=2[N:19]=[C:32]1[C:31]1[CH:34]=[C:27]([C:24]2[CH:23]=[N:22][N:21]([CH3:20])[C:25]=2[CH3:26])[CH:28]=[CH:29][C:30]=1[N:35]1[CH:39]=[N:38][CH:37]=[N:36]1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 58541886HCID 58541886, compoundHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamine

Product 1

HCID 53238529HCID 53238529, compoundYield 41.2%

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 (10 mL) is added crude 5-(1,5-dimethyl-1H-pyrazol-4-yl)-2-[1,2,4]triazole-1-yl-benzaldehyde (112 mg, 0.42 mmol) at room temperature. Oxone (239 mg, 0.39 mmol) in H2O (1 mL) is added and the solution is stirred at the same temperature for 3 hours. Sat. sodium thiosulfate (10 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL). The combined organic layer is dried with MgSO4 (1 g) and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (81 mg, 41%). LCMS (ESMS): m/z: 505.40 (M++1).

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried with MgSO4 (1 g)
  3. filtrationis filtered
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-1c8c490471894cebbdebc8846a9753aa
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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