Ammonium Chloride → HCID 67089157, compound

HRID 1943929Notes

Reaction equation

HRID 1943929 reaction equation
[Cl-].[NH4+].[CH3:3][O:4][C:5]1[CH:28]=[CH:27][C:8]([CH2:9][N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N+:19]([O-])=O)[CH:18]=[C:13]3[C:12]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[N:11]2)=[CH:7][CH:6]=1>CCO.O.CCOC(C)=O.O.[Fe]>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:19])[CH:18]=[C:13]3[C:12]([O:22][CH2:23][CH2:24][O:25][CH3:26])=[N:11]2)=[CH:27][CH:28]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 67089033HCID 67089033, compound

Product 1

HCID 67089157HCID 67089157, compoundYield 92%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
85 °C

Procedure

Fe (0) (0.251 g, 4.49 mmol) and ammonium chloride (0.600 g, 11.2 mmol) were added to 1-(4-methoxybenzyl)-3-(2-methoxyethoxy)-5-nitro-1H-pyrazolo[3,4-b]pyridine (402 mg, 1.12 mmol) in EtOH (8 mL) and water (3.7 mL). The mixture was stirred at 85° C. for 5 hours. The mixture was diluted with EtOAc-water and filtered through GF/F paper. The filtrate was diluted with aqueous bicarbonate and extracted with EtOAc (3×12 mL), dried over sodium sulfate, decanted and concentrated to provide 1-(4-methoxybenzyl)-3-(2-methoxyethoxy)-1H-pyrazolo[3,4-b]pyridin-5-amine (338 mg, 92%).

Workup

  1. filtrationfiltered through GF/F paper
  2. additionThe filtrate was diluted with aqueous bicarbonate
  3. extractionextracted with EtOAc (3×12 mL)
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1086efc467704951b523f0baa0331f3a
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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