Ammonium Chloride → HCID 21876081, compound

HRID 858504Notes

Reaction equation

HRID 858504 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3=[N:17][C:18]([CH3:22])=[CH:19][C:20]([CH3:21])=[C:15]3[N:14]=[C:13]2[CH2:23][CH3:24])=[CH:8][C:7]=1[Cl:25])=[N+]=[N-].[NH4+].[Cl-]>C(O)C.O.[Fe]>[Cl:25][C:7]1[CH:8]=[C:9]([N:12]2[C:16]3=[N:17][C:18]([CH3:22])=[CH:19][C:20]([CH3:21])=[C:15]3[N:14]=[C:13]2[CH2:23][CH3:24])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][NH2:1]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86611503HCID 86611503, compound

Product 1

HCID 21876081HCID 21876081, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of methyl 3-[4-(2-azidoethyl)-3-chlorophenyl-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (step 10, 430 mg, 1.2 mmol) in ethanol/water (4/1) were added Fe (335 mg, 6.0 mmol) and NH4Cl (409 mg, 7.8 mmol). The mixture was stirred for 1 h under reflux temperature. The solvent was removed and the residue was diluted with CH2Cl2.The mixture was washed with brine, dried (MgSO4) and concentrated to give 390 mg of title compound as orange oil.

Workup

  1. temperatureunder reflux temperature
  2. customThe solvent was removed
  3. additionthe residue was diluted with CH2Cl2
  4. washThe mixture was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3237869437634f079f63d0555713bd84
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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