Acetic Acid → HCID 57742362, compound

HRID 655303Notes

Reaction equation

HRID 655303 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[N:14]([NH2:19])[C:15]([NH2:18])=[N:16][N:17]=1)=[CH:7][CH:6]=2.[CH:20]([CH:22]=O)=O.C(O)(=O)C>O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[N:14]3[N:19]=[CH:20][CH:22]=[N:18][C:15]3=[N:16][N:17]=1)=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7860GlyoxalHCID 57742338HCID 57742338, compound

Product 1

HCID 57742362HCID 57742362, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(3-bromo-quinolin-6-ylmethyl)-[1,2,4]triazole-3,4-diamine (977 mg, 3 mmol), glyoxal (40% solution in water, 5 mL), acetic acid (10 mL) and water (2 mL) was stirred at ambient temperature for 18 hours. After such time the mixture was filtered and the filtrate was concentrated onto silica gel and via flash column chromatography (SiO2 12 g, dichloromethane/CH3OH, 0-10%) to return the title compound a white solid (298 mg, 29%). Analytical data presented in Table 1.

Workup

  1. filtrationAfter such time the mixture was filtered
  2. concentrationthe filtrate was concentrated onto silica gel and via flash column chromatography (SiO2 12 g, dichloromethane/CH3OH, 0-10%)

Sources & evidence

ORD record
ord-a46a1aac0b64403fa16bdb875cc8fcba
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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