Triethylamine → HCID 68663927, compound

HRID 452618Notes

Reaction equation

HRID 452618 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[C:20]1([CH2:26][CH2:27][C:28](Cl)=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.C(OCC)(=O)C>[C:20]1([CH2:26][CH2:27][C:28]([NH:1][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][N:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 7015521Ethyl 2-aminopyridine-4-carboxylate

Product 1

HCID 68663927HCID 68663927, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-aminoisonicotinate (4.50 g, 27.08 mmol) and triethylamine (9.0 mL, 64.93 mmol) in tetrahydrofuran (100 mL) was added 3-phenylpropanoyl chloride (8.3 mL, 56.11 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=95/5-0/100) and recrystallized from hexane/ethyl acetate to give the title compound (6.85 g, yield 85%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1cd089dabeab4907abd55fbb96b0bf8f
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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