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

HRID 383090Notes

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+]>>[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

Reactant 4

HCID 104392-Aminopyridine

HCID 516892Sodium Bicarbonate

HCID 5003444Sodium cyanoborohydride

HCID 105712674-Formyl-2-phenylbenzoyl methionine methyl ester

Product 1

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

Procedure

A mixture of the resultant aldehyde from Example 16E (1.0 equivalent), 2-aminopyridine (1.0 equivalent) and NaCNBH3 (1.5 equivalents) in methanouacetic 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

extractionextracted into ethyl acetate which
customis dried
customevaporated

Sources & evidence

ORD record: ord-d796c42b18b84403bb0446c02fd81d18
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310095B1

Reaction notes

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