Triethylamine → 1-[5-(3-Cyano-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-3-[2-(5-ethyl-oxazol-2-yl)-ethyl]-urea

HRID 601638Notes

Reaction equation

HRID 601638 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([NH:18][C:19]([N:21]3[CH:25]=[CH:24]N=C3)=[O:20])=[N:15][C:14]=2[CH3:26])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10])#[N:2].[CH2:27]([C:29]1[O:33][C:32](CCN)=[N:31][CH:30]=1)[CH3:28].C(N(CC)CC)C>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][C:16]([NH:18][C:19]([NH:21][CH2:25][CH2:24][C:32]3[O:33][C:29]([CH2:27][CH3:28])=[CH:30][N:31]=3)=[O:20])=[N:15][C:14]=2[CH3:26])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 115428012-(5-Ethyloxazol-2-yl)ethylamineHCID 11603446Imidazole-1-carboxylic acid [5-(3-cyano-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide

Product 1

HCID 115907001-[5-(3-Cyano-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-3-[2-(5-ethyl-oxazol-2-yl)-ethyl]-urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of imidazole-1-carboxylic acid [5-(3-cyano-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-amide (Intermediate BD) (0.05 g, 1.29 mmol) in DMF (1.5 ml) under an inert atmosphere is added 2-(5-ethyl-oxazol-2-yl)-ethylamine (Amine) (0.018 g, 1.29 mmol) followed by triethylamine (0.02 ml, 0.14 mmol). The reaction mixture is heated to 70° C. for 2.5 hours and then allowed to cool to room temperature. The solvent is removed in vacuo and the resulting crude residue is dissolved in THF and passed through a 0.5 g polymer supported isocyanate resin (pre-washed with THE). The solution is concentrated in vacuo and the crude residue is dissolved in DCM and washed with water, brine, dried over MgSO4 and concentrated in vacuo again. Triturating with ether affords the titled compound as a yellow solid.

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent is removed in vacuo
  3. dissolutionthe resulting crude residue is dissolved in THF
  4. washpre-washed with THE)
  5. concentrationThe solution is concentrated in vacuo
  6. dissolutionthe crude residue is dissolved in DCM
  7. washwashed with water, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo again
  10. customTriturating with ether

Sources & evidence

ORD record
ord-7849fa5456544017b5f8fba858f6346b
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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