Sodium Dithionite → HCID 178432933, compound

HRID 63594Notes

Reaction equation

HRID 63594 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[N:23]=[C:22]([CH3:24])[O:21][N:20]=3)[CH2:14][CH2:13]2)=[C:4]([N+:9]([O-])=O)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:25][N:26]1[CH:30]=[C:29]([CH:31]=O)[C:28]([CH3:33])=[N:27]1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CCO>[Cl:1][C:2]1[C:3]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[N:23]=[C:22]([CH3:24])[O:21][N:20]=3)[CH2:14][CH2:13]2)=[C:4]2[N:9]=[C:31]([C:29]3[C:28]([CH3:33])=[N:27][N:26]([CH3:25])[CH:30]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24489Sodium DithioniteHCID 8472851,3-dimethyl-1H-pyrazole-4-carbaldehydeHCID 714814732-Amino-5-chloro-4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)methylpiperazin-1-yl)-3-nitropyridine

Product 1

HCID 178432933HCID 178432933, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-chloro-4-(4-((5-methyl-1,2,4-oxadiazol-3-yl)methyl)piperazin-1-yl)-3-nitropyridin-2-amine (60.0 mg, 0.170 mmol) and 1,3-dimethyl-1H-pyrazole-4-carbaldehyde (22.2 mg, 0.179 mmol) in EtOH (3.8 mL) was added 1M Na2S2O4 (0.678 mL, 0.678 mmol, freshly prepared) and the solution was heated to 80° C. and stirred for 16 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 (3×14) eluting with MeOH/CH2Cl2 (5-7.5%) to yield the title compound as a pale yellow solid. Recrystallisation in EtOAc/Et2O gave the title compound (20 mg, 27%) as an off white solid. The filtrate was concentrated in vacuo, an additional amount of title compound (12 mg, 16%) as a pale yellow solid. 1H-NMR (500 MHz, CDCl3) 2.60 (s, 3H, CH3), 2.62 (s, 3H, CH3), 2.81 (app t, J=4.5 Hz, 4H, CH2), 3.76 (s, 2H, —CH2—), 3.87 (app s, 4H, CH2), 3.90 (s, 3H, NCH3), 7.77 (br s, 1H, CHar), 7.96 (br S, 1H, CHar), 12.18 (s, 1H, NH);

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-517606a3f48a480f84bde4af3f0571c6
Source dataset
uspto-grants-2016_09
Patent number
US09447092B2

Reaction notes

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