N,N-Dimethyl-beta-alaninamide → 3-{3-[5-(2,6-Dimethyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-ureido}-N,N-dimethyl-propionamide

HRID 1951226Notes

Reaction equation

HRID 1951226 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14]([N:16]3[CH:20]=[CH:19]N=C3)=[O:15])=[N:10][C:9]=2[CH3:21])[CH:5]=[C:4]([CH3:22])[N:3]=1.NCC[C:26]([N:28]([CH3:30])[CH3:29])=[O:27]>CN(C=O)C>[CH3:22][C:4]1[CH:5]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:15])[NH:16][CH2:20][CH2:19][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[N:10][C:9]=2[CH3:21])[CH:7]=[C:2]([CH3:1])[N:3]=1

Participants

4

Reactant 2

HCID 12742480N,N-Dimethyl-beta-alaninamideHCID 86610333Imidazole-1-carboxylic acid [5-(2,6-dimethyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-amide

Product 1

HCID 112913913-{3-[5-(2,6-Dimethyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-ureido}-N,N-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of imidazole-1-carboxylic acid [5-(2,6-dimethyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]-amide (Intermediate BA) (0.05 g, 0.16 mmol) in DMF (1.5 ml) under an inert atmosphere is added 3-amino-N,N-dimethyl-propionamide (Amine) (0.018 g, 0.16 mmol). The reaction mixture is stirred at room temperature for 18 hours. The solvent is removed in vacuo and the resulting crude residue is dissolved in THF and passed through a plug of polymer supported isocyanate resin (0.5 g, pre-washed with THF). The solution is concentrated in vacuo and the crude residue is trituated with ether-ethyl acetate to afford the titled compound as a yellow solid.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resulting crude residue is dissolved in THF
  3. concentrationThe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-dc7d044396cb4061bbc5120b444a773b
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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