N,N-Dimethyl-beta-alaninamide → N,N-Dimethyl-3-[3-(4-methyl-5-pyridin-4-yl-thiazol-2-yl)-ureido]-propionamide

HRID 1951190Notes

Reaction equation

HRID 1951190 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:13][C:14]([N:16]2[CH:20]=[CH:19]N=C2)=[O:15])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.NCC[C:24]([N:26]([CH3:28])[CH3:27])=[O:25]>O1CCOCC1>[CH3:27][N:26]([CH3:28])[C:24](=[O:25])[CH2:19][CH2:20][NH:16][C:14]([NH:13][C:4]1[S:5][C:6]([C:7]2[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=2)=[C:2]([CH3:1])[N:3]=1)=[O:15]

Participants

4

Reactant 2

HCID 12742480N,N-Dimethyl-beta-alaninamideHCID 86610330Imidazole-1-carboxylic acid (4-methyl-5-pyridin-4-yl-thiazol-2-yl)-amide

Product 1

HCID 11382028N,N-Dimethyl-3-[3-(4-methyl-5-pyridin-4-yl-thiazol-2-yl)-ureido]-propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of imidazole-1-carboxylic acid (4-methyl-5-pyridin-4-yl-thiazol-2-yl)-amide (example 18a) (0.15 g, 0.526 mmol) in dioxane (10 ml) is added 3-amino-N,N-dimethyl-propionamide (0.046 g, 0.526 mmol) in one portion. The reaction mixture is heated to reflux for 2 hours. The reaction mixture is allowed to cool to room temperature and the solvent is removed in vacuo. Trituration with ether/ethyl acetate yields the titled compound as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2 hours
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-e6a27ac5c6e64366ba6f3da6435007cd
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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