Methyl 2-aminopyridine-4-carboxylate → HCID 20275365, compound

HRID 370738Notes

Reaction equation

HRID 370738 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:12]([S:15][CH2:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18](O)=[O:19])(=[O:14])[CH3:13].NC1N=CC=CC=1C(OC)=O>N1C=CC=CC=1>[C:12]([S:15][CH2:16][CH:17]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:18]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:19])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 351633Methyl 2-aminopyridine-3-carboxylateHCID 99917962-[(Acetylthio)methyl]-3-phenylpropionic Acid2×

Product 1

HCID 20275365HCID 20275365, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 1, but substituting an equivalent amount of methyl 2-amino-isonicotinate and 2-acetylthiomethyl-3-phenyl-propionic acid respectively for methyl 2-amino-nicotinate and 2-acetylthiomethyl-3-phenyl-propionic acid, using pyridine as reaction solvent, maintaining the reaction mixture at 50°-60° C. for five hours and purifying by chromatography on silica gel column (eluent, petroleum ether/ether 7:3), methyl 2-(2-acetylthiomethyl-3-phenyl-propionamido)-isonicotinate is obtained as an oil which is transformed into the corresponding hydrochloride with an alcoholic solution of hydrogen chloride; m.p. 137°-139° C., from acetone/ether.

Workup

  1. customas reaction solvent
  2. temperaturemaintaining the reaction mixture at 50°-60° C. for five hours
  3. custompurifying by chromatography on silica gel column (eluent, petroleum ether/ether 7:3)

Sources & evidence

ORD record
ord-66ffdc42ad014c4a885ea754e250889e
Source dataset
uspto-grants-1985_07
Patent number
US04528296

Reaction notes

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