2-Aminopyridine → 4-[(2-Aminopyridyl)methylene]-2-phenylbenzoylmethionine methyl ester

HRID 325219Notes

Reaction equation

HRID 325219 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[CH:9][C:8]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CO.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10](=[CH:13][C:33]2[C:28]([NH2:27])=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:9][C:8]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 105712674-Formyl-2-phenylbenzoyl methionine methyl ester

Product 1

HCID 865867874-[(2-Aminopyridyl)methylene]-2-phenylbenzoylmethionine methyl ester

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

A mixture of the resultant aldehyde from Example 16E (1.0 equivalent), 2-aminopyridine (1.0 equivalent) and NaCNBH3 (1.5 equivalents) in methanol/acetic acid is stirred until the reaction is judged complete by TLC analysis. The mixture is poured into aqueous NaHCO3 and extracted into ethyl acetate which is dried and evaporated. Chromatography of the residue on silica gel affords the title compound.

Workup

  1. extractionextracted into ethyl acetate which
  2. customis dried
  3. customevaporated

Sources & evidence

ORD record
ord-3528ab9fdc4c4e1cad3596a67a81fd56
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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