Ammonium Chloride → HCID 21876081, compound

HRID 1454696Notes

Reaction equation

HRID 1454696 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-eae3ad83575d4958a9e2e105cee2ff81
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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