Ammonia → HCID 59592787, compound

HRID 2261012Notes

Reaction equation

HRID 2261012 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH2:20][N:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=3)=[C:5]2[CH:4]=[N:3]1.O.O.Cl[Sn]Cl.N>CCO>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([CH2:20][N:21]3[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]3)=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)=[C:5]2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 61436Stannous chloride dihydrateHCID 59592761HCID 59592761, compound2×

Product 1

HCID 59592787HCID 59592787, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In analogy to GP3, 1.06 g of 1-methyl-6-(4-methyl-piperazin-1-ylmethyl)-4-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine (Intermediate 17.8; 2.89 mmol, 1 eq.) were dissolved in 15 mL EtOH, treated with 3.26 g SnCl2.2H2O (14.46 mmol, 5 eq.) and stirred at reflux for 2 h. The reaction was poured into conc. NH3, partitioned between CH2Cl2 and water, the aqueous layer was re-extracted, the combined organic layers were dried and concentrated in vacuo to yield 663 mg of the crude aniline (1.97 mmol, 68% yield).

Workup

  1. temperatureat reflux for 2 h
  2. custompartitioned between CH2Cl2 and water
  3. extractionthe aqueous layer was re-extracted
  4. customthe combined organic layers were dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fd1925b851c4131b220dfab897bd161
Source dataset
uspto-grants-2010_12
Patent number
US07846928B2

Reaction notes

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