Triethylamine → HCID 66707604, compound

HRID 1848350Notes

Reaction equation

HRID 1848350 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][NH2:16])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.CCN(CC)CC.[C:24](Cl)(=[O:28])[CH:25]([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][NH:16][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 516892Sodium BicarbonateHCID 58074577HCID 58074577, compound

Product 1

HCID 66707604HCID 66707604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere C-[1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropyl]-methylamine (0.05 g, 0.23 mmol) was dissolved in THF (1 mL) and Et3N (0.048 mL, 0.35 mmol). Isobutyryl chloride (0.03 mL, 0.29 mmol) was added. Stirring for 30 min. Aq. NaHCO3 and H2O was added. The aqueous phase was extracted with DCM (×3). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo to afford N-[1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-isobutyramide as a solid.

Workup

  1. extractionThe aqueous phase was extracted with DCM (×3)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21fac9c0db424d858943bc2a05e99014
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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