Triethylamine → N-[5-(4-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-isobutyramide

HRID 1054341Notes

Reaction equation

HRID 1054341 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16]([NH2:18])[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH:26]([C:29](Cl)=[O:30])([CH3:28])[CH3:27]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:29](=[O:30])[CH:26]([CH3:28])[CH3:27])[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 62325Isobutyryl chlorideHCID 591864185-(4-Methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 42599883N-[5-(4-Methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-isobutyramide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the 5-(4-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.07 g, 0.291 mmol) in dry acetonitrile (2 mL) was added triethylamine (0.12 mL, 0.874 mmol) followed by isopropanecarbonyl chloride (0.046 mL, 0.437 mmol). The reaction mixture was then allowed to warm to ambient temperature overnight. Further triethylamine (1.5 eq) and acid chloride (1.2 eq) were added to ensure complete reaction. The solvent was then removed and 3 mL of methanol-ammonia 7M was added to the crude and the mixture was stirred 6 h. The solution was concentrated under reduced pressure and the crude was purified by preparatory HPLC. LCMS method: 2, RT: 4.33 min, MI: 311 [M+1]. NMR 1H (DMSO): 1.05 (d, 6H), 2.65-2.75 (m, 1H), 3.86 (s, 3H), 7.06 (d, 2H), 7.19 (d, 1H), 7.57-7.69 (m, 2H), 7.95 (d, 2H), 10.68 (brs, 1H).

Workup

  1. customreaction
  2. customThe solvent was then removed
  3. addition3 mL of methanol-ammonia 7M was added to the crude
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe crude was purified by preparatory HPLC

Sources & evidence

ORD record
ord-dc1e86ac3b7a420b88a670bea4d73fcc
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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