3-Aminopropylphosphonic acid → 3-((6-Phenyl-5-(4-propylphenyl)pyridin-2-yl)methylamino)propylphosphonic Acid

HRID 12551Notes

Reaction equation

HRID 12551 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([CH:13]=O)[CH:10]=[CH:9][C:8]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][CH2:25][CH2:26][CH2:27][P:28](=[O:31])([OH:30])[OH:29].[BH3-]C#N.[Na+]>CO>[C:1]1([C:7]2[N:12]=[C:11]([CH2:13][NH:24][CH2:25][CH2:26][CH2:27][P:28](=[O:29])([OH:31])[OH:30])[CH:10]=[CH:9][C:8]=2[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 975873-Aminopropylphosphonic acidHCID 5003444Sodium cyanoborohydrideHCID 866190756-Phenyl-5-(4-propylphenyl)pyridine-2-carbaldehyde2×

Product 1

HCID 497872503-((6-Phenyl-5-(4-propylphenyl)pyridin-2-yl)methylamino)propylphosphonic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Following General Procedure M, 6-phenyl-5-(4-propylphenyl)pyridine-2-carbaldehyde (Compound 59, 74 mg, 0.25 mmol), (3-amino-propyl)phosphonic acid (34 mg, 0.25 mmol), Bu4NOH (0.25 ml, 0.25 mmol, 1M in MeOH) and NaCNBH3 (15 mg, 0.25 mmol) in MeOH (5 ml) were reacted to produce the title compound as a white solid.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-7379c5469345430caa35630f18548b1c
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Reaction notes

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