Ammonia → HCID 22663070, compound

HRID 731601Notes

Reaction equation

HRID 731601 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[N: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.[Cl-].[Zn+2].[Cl-]>[O:15]=[C:14]([C:3]1[C:4]2[C:9](=[CH:8][N:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[C:13]([NH2:19])=[O:17]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 1049PyridineHCID 92196-AzaindoleHCID 65578Oxalyl chlorideHCID 178418373HCID 178418373, compound

Product 1

HCID 22663070HCID 22663070, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 6-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 remove the solvent and excess oxalyl chloride. The resultant residue is dissolved in CH3CN and pyridine (1.6 eq.), treated with ammonia (2 eq., solution in dioxane), stirred for 1 h and concentrated in vacuo. This residue 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 remove the solvent and excess oxalyl chloride
  5. dissolutionThe resultant residue is dissolved in CH3CN
  6. stirringstirred for 1 h
  7. concentrationconcentrated in vacuo
  8. customThis residue is purified by chromatography [silica gel, CH2Cl2/methanol (containing 5% ammonium hydroxide) as eluent]

Sources & evidence

ORD record
ord-ab12c65e53944ac5aaee91d604c50653
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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