Sodium Dithionite → HCID 178434001, compound

HRID 63592Notes

Reaction equation

HRID 63592 reaction equation
[O:1]1[CH:5]=[N:4][C:3]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]3[C:18]([Cl:19])=[CH:17][N:16]=[C:15]([NH2:20])[C:14]=3[N+:21]([O-])=O)[CH2:9][CH2:8]2)=[N:2]1.[CH3:24][N:25]1[CH:29]=[C:28]([CH:30]=O)[C:27]([CH3:32])=[N:26]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO>[Cl:19][C:18]1[C:13]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:3]3[N:4]=[CH:5][O:1][N:2]=3)[CH2:8][CH2:9]2)=[C:14]2[N:21]=[C:30]([C:28]3[C:27]([CH3:32])=[N:26][N:25]([CH3:24])[CH:29]=3)[NH:20][C:15]2=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 8472851,3-dimethyl-1H-pyrazole-4-carbaldehydeHCID 714814725-Chloro-3-nitro-4-[4-(1,2,4-oxadiazol-3-ylmethyl)-1-piperazinyl]-2-pyridinamine

Product 1

HCID 178434001HCID 178434001, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(4-((1,2,4-oxadiazol-3-yl)methyl)piperazin-1-yl)-5-chloro-3-nitropyridin-2-amine (50.0 mg, 0.147 mmol) and 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (19.2 mg, 0.155 mmol) in EtOH (3.4 mL) was added 1M Na2S2O4 (0.588 mL, 0.588 mmol, freshly prepared) and the solution was heated to 80° C. and stirred for 15 h whilst being open to air. Once cooled, the reaction was evaporated in vacuo and the residue dry loaded onto silica. Purification was accomplished by flash chromatography on silica gel (2×14) eluting with MeOH/CH2Cl2 (5-7.5%) to yield the title compound (26 mg, 43%) as a pale yellow solid.

Workup

  1. customfreshly prepared) and the solution
  2. temperatureOnce cooled
  3. customthe reaction was evaporated in vacuo
  4. customthe residue dry
  5. customPurification
  6. washeluting with MeOH/CH2Cl2 (5-7.5%)

Sources & evidence

ORD record
ord-c35d81df4f2f4ec7827a83110a06b2d5
Source dataset
uspto-grants-2016_09
Patent number
US09447092B2

Reaction notes

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