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

HRID 356330Notes

Reaction equation

HRID 356330 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-ed0ff7fd535f4edd8ee046676deb0319
Source dataset
uspto-grants-1998_11
Patent number
US05834501

Reaction notes

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