Acetic Acid → 1-(2-fluorobenzyl)-1H-indazole-3-carboximidamide hydrochloride

HRID 2307852Notes

Reaction equation

HRID 2307852 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]#[N:18])=[N:9]1.C(O)(=O)C.[NH4+:27].[Cl-:28]>CO>[Cl-:28].[F:4][C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]([NH2:27])=[NH2+:18])=[N:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium Methoxide2×HCID 113910691-(2-Fluorobenzyl)-3-cyanoindazole

Product 1

HCID 114039631-(2-fluorobenzyl)-1H-indazole-3-carboximidamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
40 °C

Procedure

A sodium methoxide solution, which had been prepared from 190 mg (8.26 mmol) of NaOMe and 30 ml of abs. methanol, was added to a solution of 20.0 g (97.7 mmol) of 1-(2-fluorobenzyl)-3-cyanoindazole (from Example IX) in 200 ml of methanol, and the mixture was stirred at 40° C. for 22 h. After addition of 0.46 ml of acetic acid and 4.30 g of NH4Cl, the mixture was stirred at 40° C. for another 24 h and subsequently concentrated to dryness using a rotary evaporator. The residue was taken up in acetone and the remaining precipitate was filtered off with suction, giving, after drying under high vacuum, the product in the form of a light-beige powder.

Workup

  1. stirringthe mixture was stirred at 40° C. for another 24 h
  2. concentrationsubsequently concentrated to dryness
  3. customa rotary evaporator
  4. filtrationthe remaining precipitate was filtered off with suction
  5. customgiving
  6. customafter drying under high vacuum

Sources & evidence

ORD record
ord-49d5eca7ba544da2ae336285be32e86a
Source dataset
uspto-grants-2004_12
Patent number
US06833364B1

Reaction notes

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