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

HRID 1593507Notes

Reaction equation

HRID 1593507 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-15bacb3c26e2490a91515fb0c756cb72
Source dataset
uspto-grants-2007_11
Patent number
US07297705B2

Reaction notes

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