Glycolic Acid → 3h-Imidazo[4,5-b]pyridine-2-methanol,3-methyl-5-(1-methylethoxy)-

HRID 1953744Notes

Reaction equation

HRID 1953744 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][CH3:13])=[N:4][C:5]([O:8][CH:9]([CH3:11])[CH3:10])=[CH:6][CH:7]=1.[C:14]([OH:18])(=O)[CH2:15]O>>[CH:9]([O:8][C:5]1[N:4]=[C:3]2[N:12]([CH3:13])[C:15]([CH2:14][OH:18])=[N:1][C:2]2=[CH:7][CH:6]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 108212696-Isopropoxy-N2-methylpyridine-2,3-diamine

Product 1

HCID 108228683h-Imidazo[4,5-b]pyridine-2-methanol,3-methyl-5-(1-methylethoxy)-Yield 25%

Procedure

A procedure similar to that described in Preparation 43 was repeated, except that 1.90 g of 3-amino-6-isopropoxy-2-methylaminopyridine (prepared as described in Preparation 101), and 2.39 g of glycolic acid were used, and that the product was purified by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and methanol, to give 0.58 g of the title compound, melting at 125-127° C.

Workup

  1. customA procedure similar to that described in Preparation 43
  2. customthat the product was purified by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-134c8397fc714debbddd383b04411ca8
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

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