Acetic Acid → ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate

HRID 896229Notes

Reaction equation

HRID 896229 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=NC=CC=[C:8]2[C:7](C(=N)OC)=[N:6]1.[C:22](O)(=[O:24])[CH3:23].[Cl-].[NH4+:27].[CH3:28][OH:29]>>[NH2:27][C:9]1[N:5]([CH2:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=2[F:1])[N:6]=[C:7]([C:28]([O:24][CH2:22][CH3:23])=[O:29])[CH:8]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 25517Ammonium ChlorideHCID 11243078Methyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carbiMidate

Product 1

HCID 11391384ethyl 5-amino-1-(2-fluorobenzyl)-1H-pyrazole-3-carboxylate

Procedure

The solution of methyl (2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidate in methanol obtained from example 2 E) is mixed with 33.76 g (32.19 ml, 562 mmol) of glacial acetic acid and 9.28 g (173 mmol) of ammonium chloride and stirred under reflux overnight. The solvent is evaporated in vacuo, the residue is thoroughly triturated with acetone, and the precipitated solid is filtered off with suction.

Workup

  1. temperatureunder reflux overnight
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is thoroughly triturated with acetone
  4. filtrationthe precipitated solid is filtered off with suction

Sources & evidence

ORD record
ord-68e09150f4784ad795f17ea1d0f31521
Source dataset
uspto-grants-2005_07
Patent number
US06919345B2

Reaction notes

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