Oxazole → 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-cyclohexylthiazole

HRID 254836Notes

Reaction equation

HRID 254836 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][CH2:24][C:25]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=O)=O)[C:9]=2[CH3:33])=[CH:4][CH:3]=1.O1C=CN=C1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:48])=CC=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[S:48][C:25]([CH:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:24][N:23]=3)[C:9]=2[CH3:33])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9255OxazoleHCID 87949Lawesson's reagentHCID 668447715-(4-chlorophenyl)-N-(2-cyclohexyl-2-oxoethyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide

Product 1

HCID 668441472-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-cyclohexylthiazoleYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-chlorophenyl)-N-(2-cyclohexyl-2-oxoethyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (116 mg, 0.23 mmol) obtained in Step 3 of preparation of oxazole was added to a microwave reactor containing Lawesson's reagent (186 mg, 0.46 mmol) in THF (2 mL). The capped reactor was placed in a microwave reactor and the mixture was irradiated at 1860° C. for 30 min. The reaction product was purified by reverse-phase prep HPLC to provide the title compound (88 mg, 76%) as white solid.

Workup

  1. additionwas added to a microwave reactor
  2. customThe capped reactor was placed in a microwave reactor
  3. customthe mixture was irradiated at 1860° C. for 30 min
  4. customThe reaction product was purified by reverse-phase prep HPLC

Sources & evidence

ORD record
ord-e88b1e74198f46f8926f7dca03a1979d
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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