Methylamine → 2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methylamide

HRID 2112933Notes

Reaction equation

HRID 2112933 reaction equation
C[O:2][C:3]([C:5]1[N:10]2[N:11]=[C:12]([NH:14][C:15]([NH:17][CH2:18][CH3:19])=[O:16])[N:13]=[C:9]2[CH:8]=[C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=1)=O.[CH3:26][NH2:27]>CCO>[CH3:26][NH:27][C:3]([C:5]1[N:10]2[N:11]=[C:12]([NH:14][C:15]([NH:17][CH2:18][CH3:19])=[O:16])[N:13]=[C:9]2[CH:8]=[C:7]([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 445719542-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methyl ester

Product 1

HCID 445720012-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methylamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-Ethyl-ureido)-7-pyridin-3-yl-[1,2,4]triazolo[1,5-a]pyridine-5-carboxylic acid methyl ester, prepared as in Example 6, (46 mg, 0.14 mmol) was suspended/dissolved in 33% methylamine in EtOH (15 mL), then stirred overnight at room temperature. After this time the reaction mixture was concentrated to a volume of ca 5 mL, then diluted with Et2O (5 mL). The resulting precipitate was isolated by filtration and washed well with Et2O to give the final product mp. >300° C. LCMS (APCI+) 340.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated to a volume of ca 5 mL
  2. additiondiluted with Et2O (5 mL)
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed well with Et2O

Sources & evidence

ORD record
ord-443389a7ee3040359fd7d9f20ad731df
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

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