Diisopropylethylamine → 2-Amino-8-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methyl ester

HRID 451451Notes

Reaction equation

HRID 451451 reaction equation
[Br:1][C:2]1[C:3]([NH:13][C:14]([NH:16]C(OCC)=O)=S)=[N:4][C:5]([C:8]([O:10][CH2:11]C)=[O:9])=[CH:6][CH:7]=1.Cl.NO.C([N:28](C(C)C)CC)(C)C>CO>[CH3:11][O:10][C:8]([C:5]1[N:4]2[N:28]=[C:14]([NH2:16])[N:13]=[C:3]2[C:2]([Br:1])=[CH:7][CH:6]=1)=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86656219N-(3-bromo-6-ethoxycarbonyl-pyridin-2-yl)-N'-ethoxycarbonyl-thiourea

Product 1

HCID 673372952-Amino-8-bromo-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3-bromo-6-ethoxycarbonyl-pyridin-2-yl)-N′-ethoxycarbonyl-thiourea (2 g, 5.52 mmol) in dry methanol (10 mL) were added hydroxylamine hydrochloride (1.92 g, 27.62 mmol) and diisopropyl ethylamine (2.98 mL, 16.57 mmol) under an argon atmosphere and stirred at room temperature for 4 hours. The solid was filtered and methanol (40 mL) was added to residue. The reaction mixture was heated to reflux for 12 hours. The solvent was evaporated and the title compound was obtained as off white solid (800 mg, 53%).

Workup

  1. filtrationThe solid was filtered
  2. additionmethanol (40 mL) was added to residue
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 12 hours
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6d4dedefa6ad4a879d53e05dccc0eba2
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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