Thiourea → HCID 178504254, compound

HRID 1951829Notes

Reaction equation

HRID 1951829 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]2[CH:49]=[CH:48][C:11]([CH2:12][C:13]3[N:14]([C:26]4[CH:27]=[C:28]([N:32]5[S:36](=[O:38])(=[O:37])[N:35]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:34](=[O:47])[CH2:33]5)[CH:29]=[CH:30][CH:31]=4)[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[N:17]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.NC(N)=[S:52]>C(O)C.O.CCOC(C)=O>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:16]1[N:17]=[C:13]([CH2:12][C:11]2[CH:48]=[CH:49][C:8]([C:5]3[N:6]=[N:7][C:2]([SH:52])=[CH:3][CH:4]=3)=[CH:9][CH:10]=2)[N:14]([C:26]2[CH:27]=[C:28]([N:32]3[S:36](=[O:38])(=[O:37])[N:35]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:34](=[O:47])[CH2:33]3)[CH:29]=[CH:30][CH:31]=2)[CH:15]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 86614317HCID 86614317, compound

Product 1

HCID 178504254HCID 178504254, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 22728543Water ethylacetateSolvent

Procedure

5-{3-[2-[4-(6-Chloro-pyridazin-3-yl)-benzyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanyl-ethoxymethyl)-[1,2,5]thiadiazolidin-3-one (76 mg, 0.1 mmol) was dissolved in 1 mL dry ethanol. Thiourea (76 mg, 1 mmol) was added and the mixture was refluxed under nitrogen over night. At completion, the reaction mixture was then diluted with water/EtOAc. The combined organic layer was washed with water, and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give 5-(3-{4-(2,4-dichloro-phenyl)-2-[4-(6-mercapto-pyridazin-3-yl)-benzyl]-imidazol-1-yl}-phenyl)-1,1-dioxo-2-(2-trimethylsilanyl-ethoxymethyl)-[1,2,5]thiadiazolidin-3-one, which was then treated as described in general procedure K using 1-bromo-2-cyclohexylethane (79 μL, 0.5 mmol) to give 5-{3-[2-{-4-[6-(2-cyclohexyl-ethylsulfanyl)-pyridazin-3-yl]-benzyl}-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanyl-ethoxymethyl)-[1,2,5]thiadiazolidin-3-one.

Workup

  1. temperaturethe mixture was refluxed under nitrogen over night
  2. washThe combined organic layer was washed with water, and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2698c91054ac4aeca552465e00707306
Source dataset
uspto-grants-2013_03
Patent number
US08404731B2

Reaction notes

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