Methylamine → 1-Methyl-3-(4-methyl-5-pyridin-4-yl-thiazol-2-yl)-urea

HRID 1951185Notes

Reaction equation

HRID 1951185 reaction equation
CN.[CH3:3][C:4]1[N:5]=[C:6]([NH:15][C:16]([N:18]2C=CN=[CH:19]2)=[O:17])[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1>O.CN(C=O)C>[CH3:19][NH:18][C:16]([NH:15][C:6]1[S:7][C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:4]([CH3:3])[N:5]=1)=[O:17]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 86610330Imidazole-1-carboxylic acid (4-methyl-5-pyridin-4-yl-thiazol-2-yl)-amide

Product 1

HCID 866103291-Methyl-3-(4-methyl-5-pyridin-4-yl-thiazol-2-yl)-urea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methylamine (0.030 ml of a 40% w/w/solution in water, 0.351 mmol) is added to a stirred suspension of imidazole-1-carboxylic acid (4-methyl-5-pyridin-4-yl-thiazol-2-yl)-amide (18a) (0.1 g, 0.351 mmol) in DMF (3 ml). The reaction mixture is stirred at room temperature for 1 hour and then the solvent is removed in vacuo. The crude product is dissolved in THF/DMF (10:1, 3 ml) and passed through a polymer supported isocyanate resin (0.9 g, 1.1 mmol/g loading) and washed through with THF. The solution is concentrated in vacuo and the residue washed with ethyl acetate and methanol to afford the titled compound.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionThe crude product is dissolved in THF/DMF (10:1, 3 ml)
  3. washwashed through with THF
  4. concentrationThe solution is concentrated in vacuo
  5. washthe residue washed with ethyl acetate and methanol

Sources & evidence

ORD record
ord-332930a20f4148038676fee0335c1329
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

Loading…