2-Acetylthiophene → 1-[2-(4-Thiophen-2-yl-pyrimidin-2-ylamino)-ethyl]-imidazolidin-2-one

HRID 507528Notes

Reaction equation

HRID 507528 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[CH3:7].Cl.[O:10]=[C:11]1[NH:15][CH2:14][CH2:13][N:12]1[CH2:16][CH2:17][NH:18][C:19]([NH2:21])=[NH:20].[C:22](=O)([O-])[O-].[Cs+].[Cs+]>CN(C(OC)OC)C.CN1C(=O)CCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[CH:22][N:21]=[C:19]([NH:18][CH2:17][CH2:16][N:12]2[CH2:13][CH2:14][NH:15][C:11]2=[O:10])[N:20]=1

Participants

6

Reactant 3

HCID 69202-AcetylthiopheneHCID 10796Cesium carbonateHCID 178479475HCID 178479475, compound

Product 1

HCID 602042791-[2-(4-Thiophen-2-yl-pyrimidin-2-ylamino)-ethyl]-imidazolidin-2-oneYield 69.1%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 78373Dimethylformamide dimethyl acetalSolvent

Conditions

Temperature
100 °C

Procedure

1-Thiophen-2-yl-ethanone (100 mg, 0.79 mmol) was dissolved in DMF-DMA (1 mL) and heated at 100° C. for 16 h. The solution was concentrated to give a gum. This was treated with a solution of N-[2-(2-oxo-imidazolidin-1-yl)-ethyl]-guanidine hydrochloride (233 mg, 1.12 mmol) in NMP (1.5 mL), cesium carbonate (228 mg, 0.7 mmol) was added and the mixture was heated at 100° C. for 16 h. The mixture was cooled and filtered, concentrated, and purified by preparative HPLC to give the product (140 mg, 61%) as an amorphous off-white solid. MS (M+H)+ 290.

Workup

  1. concentrationThe solution was concentrated
  2. customto give a gum
  3. additionwas added
  4. temperaturethe mixture was heated at 100° C. for 16 h
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f8f171e8b83b4cc8b2836c3d632d2ddc
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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