Hydrochloric Acid → Methyl 2-amino-5H,6H,7H,8H-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate

HRID 60147Notes

Reaction equation

HRID 60147 reaction equation
CO.Cl.[NH2:4][C:5]1[N:17]=[C:8]2[CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=[CH:12][N:7]2[N:6]=1.[H][H]>[Pt](=O)=O.C(Cl)Cl>[NH2:4][C:5]1[N:17]=[C:8]2[CH2:9][CH:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][CH2:12][N:7]2[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68474008Methyl 2-amino-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 90383449Methyl 2-amino-5H,6H,7H,8H-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylateYield 107.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolvent

Procedure

Platinum(IV) oxide (3 g) was added to a mixed solution of methanol (200 ml), methylene chloride (200 ml), and concentrated hydrochloric acid (3.9 ml) containing the methyl 2-amino-[1,2,4]triazolo[1,5-a]pyridine-7-carboxylate (3.0 g) obtained in (Example 5.16) <Step 1>. The obtained mixture was stirred in a hydrogen atmosphere for 66 hours at room temperature. Thereafter, the reaction solution was filtered with Celite, and was then washed with methanol (80 ml). The filtrate was combined with the washing solution, and the thus mixed solution was then concentrated under reduced pressure. The obtained residue was subjected to azeotropy with methanol (20 ml) four times, so as to obtain the title compound (3.3 g) in the form of a light brown solid.

Workup

  1. customobtained in (Example 5.16) <Step 1>
  2. filtrationThereafter, the reaction solution was filtered with Celite
  3. washwas then washed with methanol (80 ml)
  4. concentrationthe thus mixed solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-24da4c69ab024c1685c068db7ee8ac45
Source dataset
uspto-grants-2016_09
Patent number
US09440970B2

Reaction notes

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