2-Pyridinemethanamine → HCID 18321911, compound

HRID 613592Notes

Reaction equation

HRID 613592 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1)=[O:4].Cl.C(N=C=NCCCN(C)C)C.O[N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=N1.NCC1C=CC=CN=1>CN(C)C=O.O>[N:31]1[CH:32]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:33][NH:29][C:11]([C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:15][CH:14]=1)=[O:13]

Participants

7

Reactant 4

HCID 195092-PyridinemethanamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 113102944-(3-Methoxy-3-oxopropyl)benzoic acid

Product 1

HCID 18321911HCID 18321911, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-(methoxycarbonyl)ethyl]benzoic acid (200 mg) in N,N-dimethylformamide were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (221 mg), 1-hydroxybenzotriazole (169 mg) and 2-aminomethylpyridine (114 mg) in water bath, and the mixture was stirred for 24 hours at ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a preparative thin layer chromatography (dichloromethane:methanol=10:1, V/V) to give methyl 3-[4-(2-pyridylmethylcarbamoyl)phenyl]propionate (218 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a preparative thin layer chromatography (dichloromethane:methanol=10:1, V/V)

Sources & evidence

ORD record
ord-ff92219ec63b4edc9dffd4863f728df3
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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