Glycolic Acid → HCID 178526790, compound

HRID 2102954Notes

Reaction equation

HRID 2102954 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12](O)(=O)[CH2:13][OH:14].[NH4+].[OH-]>>[N+:9]([C:5]1[CH:6]=[C:7]2[N:8]=[C:12]([CH2:13][OH:14])[NH:1][C:2]2=[N:3][CH:4]=1)([O-:11])=[O:10]

Participants

4

Reactant 3

HCID 757Glycolic AcidHCID 14923Ammonium HydroxideHCID 34801515-Nitropyridine-2,3-diamine

Product 1

HCID 178526790HCID 178526790, compoundYield 57.9%

Conditions

Temperature
145 °C

Procedure

Solid 2,3-Diamino-5-nitropyridine (prepared according to J. Med. Chem. 1997, 40, 3679-3686; 610 mg, 0.0040 mol) and solid glycolic acid (750 mg, 0.0099 mol) were combined in a sealed tube (left open) and heated to 145° C. and stirred for approx. 30-45 min (solid fuses together, liquifies then re-solidifies). After allowing to cool to rt the solid was extracted with 1N HCl. The aqueous mixture was concentrated under vacuum to leave a crude solid that was basified using conc. NH4OH solution. The ammonia solution was concentrated under vacuum to leave a crude solid that was dry-loaded on to silica and purified by column chromatography (using the ISCO system) to give a solid (450 mg) that was used directly in the next step.

Workup

  1. wait(left open)
  2. temperatureto cool to rt the solid
  3. extractionwas extracted with 1N HCl
  4. concentrationThe aqueous mixture was concentrated under vacuum
  5. customto leave a crude solid
  6. concentrationThe ammonia solution was concentrated under vacuum
  7. customto leave a crude solid
  8. custompurified by column chromatography (

Sources & evidence

ORD record
ord-c0998290dfd54baeba88ee37e8a0d2a0
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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