Dichloromethane → Pyridine-2,4-dicarboxylic acid bis-(3-methoxy-benzylamide)

HRID 1815884Notes

Reaction equation

HRID 1815884 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][C:2]=1[C:10]([OH:12])=O.[OH2:13].ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][NH2:30].Cl.[CH3:35][N:36](C)CCCN=C=NCC.[CH2:46](Cl)Cl>>[CH3:46][O:13][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:35][NH:36][C:10]([C:2]1[CH:3]=[C:4]([C:7]([NH:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([O:25][CH3:24])[CH:27]=2)=[O:9])[CH:5]=[CH:6][N:1]=1)=[O:12]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 103652,4-Pyridinedicarboxylic acidHCID 211563-MethoxybenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 10222946Pyridine-2,4-dicarboxylic acid bis-(3-methoxy-benzylamide)Yield 76%

Procedure

To a solution of 2,4-pyridinedicarboxylic acid (1.0 g, 6.0 mmol) in methylene chloride (40 mL) was added 1-hydroxybenzotriazole hydrate (HOBt) (2.03 g, 15 mmol), 3-methoxy-benzyl amine (1.53 mL, 12.0 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC) (2.88 g, 15 mmol). The solution was stirred for 24 hours at room temperature and then evaporated at reduced pressure to give an oil. The oil was partitioned between hot ethyl acetate and hot water. The organic phase was then washed with saturated sodium bicarbonate, water, and finally brine. The organic phase was dried over magnesium sulfate and evaporated at reduced pressure to give an orange oil. This was purified by MPLC chromatography using silica gel and 1:1, hexane:ethyl acetate. The oil fractions shown by thin layer chromatography (tlc) to contain the major product were combined, and the solvent was removed by evaporation under reduced pressure to give 1.85 g (76%) of the titled compound as a clear oil. MS: M+1=406.1; Microanalysis (C23H23N3O4): Calculated (Calc'd): C=68.13, H=5.97, N=10.36. Found: C=68.05, H=5.97, N=10.23.

Workup

  1. customevaporated at reduced pressure
  2. customto give an oil
  3. customThe oil was partitioned between hot ethyl acetate and hot water
  4. washThe organic phase was then washed with saturated sodium bicarbonate, water, and finally brine
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customevaporated at reduced pressure
  7. customto give an orange oil
  8. customThis was purified by MPLC chromatography
  9. customthe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-31032048b81c473abdf311c2d4ece5f1
Source dataset
uspto-grants-2005_04
Patent number
US06881743B2

Reaction notes

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