Triethylamine → HCID 178512735, compound

HRID 2278838Notes

Reaction equation

HRID 2278838 reaction equation
Cl.[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15](=[NH:17])[NH2:16])=[N:7]1.C([N:24](CC)CC)C.O.NN>C(O)C>[F:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15](=[NH:16])[NH:17][NH2:24])=[N:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 574158441-((2-Fluorophenyl)methyl)-1H-pyrazolo(3,4-b)pyridine-3-carboximidamide hydrochloride

Product 1

HCID 178512735HCID 178512735, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

50.000 g (163.535 mmol) of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide hydrochloride were dissolved in 700 ml of ethanol, and 66.192 g (654.141 mmol) of triethylamine and 10.233 g (163.535 mmol) of hydrazine hydrate (80% strength solution in water) were added at 0° C. The mixture was stirred at RT overnight and then concentrated on a rotary evaporator. The residue was taken up in ethyl acetate and the solution was washed three times with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate and concentrated on a rotary evaporator. The residue was stirred with diethyl ether, filtered off with suction and dried under high vacuum. 46.49 g (46% of theory, 68% pure) of the title compound were obtained.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. washthe solution was washed three times with saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated on a rotary evaporator
  5. stirringThe residue was stirred with diethyl ether
  6. filtrationfiltered off with suction
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-bfb932f1374d445dbb475769fa7121e9
Source dataset
uspto-grants-2015_09
Patent number
US09133191B2

Reaction notes

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