Sodium Thiosulfate → HCID 58542016, compound

HRID 1966798Notes

Reaction equation

HRID 1966798 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.[O:20]1[C:24]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)=[CH:23][CH:22]=[N:21]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:27]1[C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[C:24]1[O:20][N:21]=[CH:22][CH:23]=1)([CH3:16])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 585418994-(2-amino-pyrimidin-5-yl)-N1-tert-butyl-benzene-1,2-diamineHCID 58541915HCID 58541915, compound

Product 1

HCID 58542016HCID 58542016, compoundYield 31.3%

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 (74 mg, 029 mmol) in DMF (10 mL) is added 2-isoxazol-5-yl-benzaldehyde (60 mg, 0.29 mmol) at room temperature. Oxone (177 mg, 0.29 mmol) in H2O (1 mL) is added and the solution is stirred at the same temperature for 3 hours. Saturated 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 (37 mg, 31%). LCMS (ESMS): m/z: 411.40 (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-6c5bb6b9d98f42abb69f8c2de66f81fe
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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