4-Aminobutylphosphonic acid → 4-((5-(4-Ethylphenyl)-6-phenylpyridin-2-yl)methylamino)butylphosphonic Acid

HRID 12550Notes

Reaction equation

HRID 12550 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH:21]=O)=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1)[CH3:2].[NH2:23][CH2:24][CH2:25][CH2:26][CH2:27][P:28](=[O:31])([OH:30])[OH:29].[BH3-]C#N.[Na+]>CO>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH2:21][NH:23][CH2:24][CH2:25][CH2:26][CH2:27][P:28](=[O:29])([OH:31])[OH:30])=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 17264-Aminobutylphosphonic acidHCID 5003444Sodium cyanoborohydrideHCID 866190745-(4-Ethylphenyl)-6-phenylpyridine-2-carbaldehyde2×

Product 1

HCID 595041654-((5-(4-Ethylphenyl)-6-phenylpyridin-2-yl)methylamino)butylphosphonic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Following General Procedure M, 5-(4-ethyl-phenyl)-6-phenyl-pyridine-2-carbaldehyde (Compound 56, 58 mg, 0.18 mmol), 4-aminobutylphosphonic acid (21 mg, 0.18 mmol), Bu4NOH (0.18 ml, 0.18 mmol, 1 M in MeOH) and NaCNBH3 (9 mg, 0.18 mmol) in MeOH (2 ml) were reacted to produce the title compound as a white solid.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-fb5a8aadbc52484ba89b37b93942889d
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Reaction notes

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