1,1'-Carbonyldiimidazole → 1,1-Dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea

HRID 253883Notes

Reaction equation

HRID 253883 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.[C:9](N1C=CN=C1)(N1C=CN=C1)=[O:10].[CH:21]1([NH:28][C@H:29]2[CH2:34][CH2:33][C@H:32](C)[CH2:31][CH2:30]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]C1>CN(C1C=CN=CC=1)C.C1COCC1>[CH:29]1([N:28]([CH:21]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:9]([NH:1][C:2]2[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=2)=[O:10])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27377982-Amino-1,3-thiazole-5-carbaldehydeHCID 178461296HCID 178461296, compound

Product 1

HCID 578834711,1-Dicyclohexyl-3-(5-formyl-thiazol-2-yl)-ureaYield 34.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-5-formylthiazole (2.56 g, 20.0 mmol), carbonyldiimidazole (3.25 g, 20.0 mmol) and a catalytic amount of DMAP were heated together in 60 mL THF at 50° C. for 3 h. To this solution was added cycloheptyl-(trans-4-methylcyclohexyl)amine (4.18 g, 20.0 mmol) and the reaction mixture was stirred for an additional 6 h at room temperature. The reaction mixture was concentrated and the crude product was purified by flash chromatography (silica, CH2Cl2-EtOAc, 4:1) to obtain 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (2.3 g, 31% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by flash chromatography (silica, CH2Cl2-EtOAc, 4:1)

Sources & evidence

ORD record
ord-0543eb7c404442a9b0b7c5acff54978d
Source dataset
uspto-grants-2011_01
Patent number
US07872139B2

Reaction notes

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