Hydrochloric Acid → HCID 22379927, compound

HRID 895565Notes

Reaction equation

HRID 895565 reaction equation
[ClH:1].Cl[CH2:3][C:4](=N)OCC.[CH2:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[N:15]=[CH:14][C:13]=1[NH2:22])[CH3:10]>CCO>[Cl:1][CH2:10][C:9]1[N:11]([CH2:3][CH3:4])[C:12]2[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[N:15]=[CH:14][C:13]=2[N:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 193264Ethyl chloroacetimidateHCID 223800053,4-Pyridinediamine, N4-ethyl-6-(trifluoromethyl)-

Product 1

HCID 22379927HCID 22379927, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The HCl salt of ethyl 2-chloro-acetimidate (3.90 g, 24.58 mmol) is added to a solution of N4-ethyl-6-trifluoromethyl-pyridine-3,4-diamine (1.44 g, 7.02 mmol) in EtOH (20 mL) and refluxed for 3 h. The reaction mixture is cooled to room temperature and concentrated under reduced pressure. The residue is diluted with CH2Cl2, washed with NaHCO3 solution, dried over Na2SO4, and concentrated to obtain 2-chloromethyl-1-ethyl-6-trifluoromethyl-1H-imidazo[4,5-c]pyridine. 1H NMR (300 MHz, CDCl3): δ 9.14(s, 1H), 7.66 (s,1H), 7.26 (s, 1H), 4.87 (s, 2H), 4.40 (t, J=7.5 Hz, 2H), 1.58 (t, J=7.5 Hz, 3H).

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is diluted with CH2Cl2
  4. washwashed with NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b5401baf530479b8251e9d5f9a4a1fe
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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