Ammonia → HCID 12146854, compound

HRID 731589Notes

Reaction equation

HRID 731589 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Mg]I.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].[N:19]1C=CC=CC=1.N>CCOCC.C(#N)C.[Cl-].[Zn+2].[Cl-]>[O:15]=[C:14]([C:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[NH:1][CH:2]=1)[C:13]([NH2:19])=[O:17]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 1049PyridineHCID 92264-AzaindoleHCID 65578Oxalyl chlorideHCID 178418373HCID 178418373, compound

Product 1

HCID 12146854HCID 12146854, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4-azaindole (1.0 eq.) in ether is treated with methyl magnesium iodide (1.1 eq.) at room temperature, stirred for 1 h, treated with zinc chloride (1.2 eq.), stirred for a further 1 h, treated with oxalyl chloride (10 eq.), stirred for 10 h and concentrated in vacuo to give a residue. The residue is dissolved in acetonitrile and pyridine (1.6 eq.), treated with ammonia (2 eq., solution in dioxane), stirred for 1 h and concentrated in vacuo. The concentrate is purified by chromatography [silica gel, CH2Cl2/methanol (containing 5% ammonium hydroxide) as eluent] to afford the title acetamide compound.

Workup

  1. stirringstirred for a further 1 h
  2. stirringstirred for 10 h
  3. concentrationconcentrated in vacuo
  4. customto give a residue
  5. stirringstirred for 1 h
  6. concentrationconcentrated in vacuo
  7. customThe concentrate is purified by chromatography [silica gel, CH2Cl2/methanol (containing 5% ammonium hydroxide) as eluent]

Sources & evidence

ORD record
ord-e082b6f3de424b228458ae69a92581f0
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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