2-Pyridinemethanamine → HCID 18321911, compound

HRID 1871092Notes

Reaction equation

HRID 1871092 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-365269bb40364de3932ba97df3d5cf7d
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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