2-Aminopyridine → 4-[(Pyridin-2-ylamino)carbonyl]-2-phenylbenzoyl methionine methyl ester

HRID 1532844Notes

Reaction equation

HRID 1532844 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([C:13](O)=[O:14])=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ON1C(=O)C2C=CC=CC=2N=N1.[NH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)=[O:14])=[CH:9][C:8]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 206228254-Carboxy-2-phenylbenzoyl methionine methyl ester

Product 1

HCID 206228404-[(Pyridin-2-ylamino)carbonyl]-2-phenylbenzoyl methionine methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the resultant acid from Example 60A (1.0 equivalent) in DMF is added 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (1.5 equivalents) followed by 2-aminopyridine (1.0 equivalent) and 1-(3-dimehtylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.5 equivalents). When judged complete by TLC analysis, the reaction is taken up in ethyl acetate which is washed by 1N HCl and saturated brine, and then is dried and evaporated. The crude reaction mixture is purified by column chromatography to afford the title product.

Workup

  1. washis washed by 1N HCl and saturated brine
  2. customis dried
  3. customevaporated
  4. customThe crude reaction mixture
  5. customis purified by column chromatography

Sources & evidence

ORD record
ord-266fd5a987724e149104c78171e4ce50
Source dataset
uspto-grants-2001_03
Patent number
US06204293B1

Reaction notes

Loading…