Ethanol → HCID 86720955, compound

HRID 524899Notes

Reaction equation

HRID 524899 reaction equation
[F:1][CH:2]([F:23])[C:3]1[CH:4]=[N:5][CH:6]=[C:7]([N:16]2C(C)=CC=C2C)[C:8]=1[N:9]1[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]1.NO.C(N(CC)CC)C.C(O)C>O>[F:23][CH:2]([F:1])[C:3]1[C:8]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:7]([NH2:16])[CH:6]=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 787HydroxylamineHCID 8471TriethylamineHCID 86720956HCID 86720956, compound

Product 1

HCID 86720955HCID 86720955, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-[3-(difluoromethyl)-5-(2,5-dimethylpyrrol-1-yl)-4-pyridyl]-4-methyl-piperazine (80 mg, 0.2497 mmol) and NH2OH (165.0 mg, 4.994 mmol) in a mixture of triethylamine (101.1 mg, 139.3 μL, 0.9988 mmol), ethanol (1 mL) and H2O (0.25 mL) was heated at reflux for 20 h. After cooling to RT the reaction was quenched by loading directly onto an SCX-2 cartridge and eluted with MeOH followed by NH3/MeOH. The basic fraction was concentrated in vacuo yielding 5-(difluoromethyl)-4-(4-methylpiperazin-1-yl)pyridin-3-amine that was used in next step without further purification. MS (ES+) 243.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. customwas quenched by loading directly onto an SCX-2 cartridge
  4. washeluted with MeOH
  5. concentrationThe basic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-5e81e56ddc834bb0abfbf7b17410adc0
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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