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

HRID 1815884노트

반응식

HRID 1815884 반응식
[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]

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-31032048b81c473abdf311c2d4ece5f1
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881743B2

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