Benzylamine → HCID 22346468, compound

HRID 897299Notes

Reaction equation

HRID 897299 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH2:15](N)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[N:24]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C>[CH2:15]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([OH:1])[C:3]([C:12]([NH2:24])=[O:14])=[CH:4][CH:5]=2)[N:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22346468HCID 22346468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 8-hydroxyquinoline-7-carboxylic acid (0.50 g, 2.64 mmol), benzylamine (0.34 g, 3.17 mmol), 1-hydroxybenzotriazole (0.45 g, 2.91 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.56 g, 2.91 mmol), and triethylamine (1.6 mL, 11.6 mmol) in DMF (15 mL) was heated at 80° C. overnight. The reaction mixture was concentrated under vacuum. The residue was dissolved in methanol and subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provide the title compound as yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in methanol
  3. customsubjected to HPLC purification on C-18 stationary phase
  4. washeluted with water/acetonitrile/TFA mobile phase
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-20960cd7161e4380b70d3b35b0d3f5e8
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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