Ammonia → 2-Oxo-2-(1H-pyrrolo[3,2-C]pyridin-3-YL)-acetamide

HRID 731597Notes

Reaction equation

HRID 731597 reaction equation
[C:1]([O-:5])(=O)[CH:2]=[O:3].N.O1CCOCC1.C(OP(O[N:22]1[C:27](=O)[C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[N:24]=N1)(OCC)=O)C.C([N:36](C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O.C(=O)([O-])[O-].[Na+].[Na+]>[O:3]=[C:2]([C:29]1[C:26]2[CH:27]=[N:22][CH:31]=[CH:32][C:25]=2[NH:24][CH:30]=1)[C:1]([NH2:36])=[O:5]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 3614358Npc324351HCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one

Product 1

HCID 226630372-Oxo-2-(1H-pyrrolo[3,2-C]pyridin-3-YL)-acetamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of methyl oxo-(1H-pyrrolo[3,2-c]-pyridin-3-yl)acetate (1 eq.) and K2CO3 (2 eq.) in methanol is stirred at room temperature for 8 h and filtered. The filtercake is air-dried to give potassium 5-azaindole 3-glyoxylate. A mixture of this glyoxylate salt, ammonia (solution in dioxane (5 eq.), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) (1 eq.) and diisopropylethylamine (DIEA) in DMF is stirred for 8 h, diluted with EtOAc and aqueous sodium carbonate. The organic phase is separated, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified over silica gel with EtOAc/MeOH as eluent to afford the title compound.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is purified over silica gel with EtOAc/MeOH as eluent

Sources & evidence

ORD record
ord-84e349e9b25042308ed9039ec70ae8c1
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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