2-Aminothiazole → 1,1-Dicyclohexyl-3-thiazol-2-yl-urea

HRID 1818261Notes

Reaction equation

HRID 1818261 reaction equation
[CH:1]1[N:5]=[C:4]([NH2:6])[S:3][CH:2]=1.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].[CH:19]1([NH:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl.C(OCC)(=O)C>[CH:26]1([N:25]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:7]([NH:6][C:4]2[S:3][CH:2]=[CH:1][N:5]=2)=[O:8])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 7582DicyclohexylamineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 111742841,1-Dicyclohexyl-3-thiazol-2-yl-urea

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of aminothiazole (50 mg, 0.5 mmol) in dichloromethane was added carbonyldiimidazole (81 mg, 0.5 mmol) and the solution stirred 2 h at room temperature. Dicyclohexylamine (1 eq) was then added and the reaction stirred overnight at room temperature. The reaction mixture is then diluted with ethyl acetate (8 mL), washed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL), dried over magnesium sulphate, concentrated in vacuo, and the residue purified by HPLC (Gilson 1, X-terra column; 0-100% CH3CN/H2O/0.1% TFA; 15 min; flow 50 ml/min) to give the title product (52 mg).

Workup

  1. stirringthe reaction stirred overnight at room temperature
  2. washwashed successively with 10% sodiumhydrogensulphate (3 mL), water (3 mL)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by HPLC (Gilson 1, X-terra column; 0-100% CH3CN/H2O/0.1% TFA; 15 min; flow 50 ml/min)

Sources & evidence

ORD record
ord-7c29f0b2d53947babee00913dae264dc
Source dataset
uspto-grants-2009_10
Patent number
US07598391B2

Reaction notes

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