3-Aminopropylphosphonic acid → (3-(((6-Phenyl-5-(p-tolyl)pyridin-2-yl)methyl)amino)propyl)phosphonic acid

HRID 12547

Reaction equation

HRID 12547 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]([CH3:21])=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][CH2:23][CH2:24][CH2:25][P:26](=[O:29])([OH:28])[OH:27].[BH3-]C#N.[Na+]>CO>[C:1]1([C:7]2[N:12]=[C:11]([CH2:13][NH:22][CH2:23][CH2:24][CH2:25][P:26](=[O:27])([OH:29])[OH:28])[CH:10]=[CH:9][C:8]=2[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[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 866190726-Phenyl-5-p-tolylpyridine-2-carbaldehyde2×

Product 1

HCID 44234515(3-(((6-Phenyl-5-(p-tolyl)pyridin-2-yl)methyl)amino)propyl)phosphonic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Following General Procedure M, 6-phenyl-5-p-tolylpyridine-2-carbaldehyde (Compound 55, 67 mg, 0.25 mmol), (3-aminopropyl)-phosphonic acid (34 mg, 0.25 mmol), Bu4NOH (0.2 ml, 0.25 mmol, 1 M in MeOH) and NaCNBH3 (15 mg, 0.25 mmol) in MeOH (3 ml) were reacted to produce the title compound as a white solid.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-022616730b0b4007b11ba681d49f496b
Source dataset
uspto-grants-2010_06
Patent number
US07728014B2

Linked notes

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