Isopropylamine → HCID 9906745, compound

HRID 496372Notes

Reaction equation

HRID 496372 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([CH3:22])=[C:6]([CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[C:7](=[O:11])[C:8]=1[O:9][CH3:10].[CH:24]([NH2:27])([CH3:26])[CH3:25].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4](=[O:23])[C:5]([CH3:22])=[C:6]([CH2:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH:27][CH:24]([CH3:26])[CH3:25])=[O:18])[C:7](=[O:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9796974HCID 9796974, compound

Product 1

HCID 9906745HCID 9906745, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)benzoic acid (85 mg, 0.27 mmol) obtained in Example 41, isopropylamine (0.035 ml, 0.41 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (78 mg, 0.41 mmol) in dry methylene chloride (3.4 ml) were stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and then was purified by a silica gel column chromatography (methylene chloride:methanol=20:1) to obtain the title compound (37 mg, 0.10 mmol, yield 37%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customwas purified by a silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-32fe133573c3472a8180a9a2dc75b670
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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