Imidazo(4,5-b)pyridine → Ammonium Hydroxide

HRID 981059Notes

Reaction equation

HRID 981059 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[N:3]=[CH:2]1.[CH:10]1([N:15]([CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25]Cl)=[N:22][CH:23]=2)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11]1>CC(N(C)C)=O>[NH4+:1].[OH-:17].[CH:27]1([N:15]([CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14]2)[C:16]([C:18]2[CH:23]=[N:22][C:21]([CH2:24][CH2:25][N:9]3[CH:8]=[CH:7][C:6]4=[N:3][CH:2]=[N:1][C:5]4=[CH:4]3)=[CH:20][CH:19]=2)=[O:17])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 2

HCID 67504Imidazo(4,5-b)pyridineHCID 20071634HCID 20071634, compound

Product 2

HCID 14923Ammonium HydroxideHCID 20071645HCID 20071645, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of imidazopyridine in dimethylacetamide under argon, N,N-dicyclopentyl-2(2-chloroethyl)-5-pyridinecarboxamide is added in one portion. The reaction temperature is slowly raised to 80°-85° C. and stirred for 24-60 hr. The reaction flask is cooled to room temperature and the solvent is removed under reduced pressure at <45° C. The residue is triturated with excess dry ether and filtered. The crude product is chromatographed on silica gel using mixtures of CH2Cl2 :MeOH:NH4OH to give the title compound.

Workup

  1. temperatureThe reaction temperature is slowly raised to 80°-85° C.
  2. customthe solvent is removed under reduced pressure at <45° C
  3. customThe residue is triturated with excess dry ether
  4. filtrationfiltered
  5. customThe crude product is chromatographed on silica gel using mixtures of CH2Cl2

Sources & evidence

ORD record
ord-d763bad1bcde4c08bbe46bf676f1cbd8
Source dataset
uspto-grants-1991_02
Patent number
US04990518

Reaction notes

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