Benzylamine → HCID 22346480, compound

HRID 897301Notes

Reaction equation

HRID 897301 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]([OH:15])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH2:16](N)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O[N:25]1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C>[CH2:16]([C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[C:9]([OH:15])[C:10]([C:12]([NH2:25])=[O:14])=[CH:11][C:2]=2[Cl:1])[N:7]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 145347675-Chloro-8-hydroxyquinoline-7-carboxylic acid

Product 1

HCID 22346480HCID 22346480, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-chloro-8-hydroxyquinoline-7-carboxylic acid (0.50 g, 2.24 mmol), benzylamine (0.29 g, 2.68 mmol), 1-hydroxy-7-azabenzotriazole (0.36 g, 2.68 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.51 g, 2.68 mmol), and triethylamine (0.62 mL, 4.47 mmol) in DMF (15 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum. The residue was dissolved in DMSO 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 DMSO
  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-cad8630b7e0a461e9bf895e0cdd472c6
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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