HCID 68591445, compound → HCID 68582730, compound

HRID 1951823Notes

Reaction equation

HRID 1951823 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:54]=[CH:53][C:16]([CH2:17][C:18]4[N:19]([C:31]5[CH:36]=[CH:35][C:34]([N:37]6[S:41](=[O:43])(=[O:42])[N:40]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:51])([CH3:50])[CH3:49])[C:39](=[O:52])[CH2:38]6)=[CH:33][CH:32]=5)[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=5[Cl:30])[N:22]=4)=[CH:15][CH:14]=3)=[N:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)(=O)C.O.CCOC(C)=O.[Fe]>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:54]=[CH:53][C:16]([CH2:17][C:18]4[N:19]([C:31]5[CH:36]=[CH:35][C:34]([N:37]6[S:41](=[O:43])(=[O:42])[N:40]([CH2:44][O:45][CH2:46][CH2:47][Si:48]([CH3:49])([CH3:50])[CH3:51])[C:39](=[O:52])[CH2:38]6)=[CH:33][CH:32]=5)[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=5[Cl:30])[N:22]=4)=[CH:15][CH:14]=3)=[N:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 68591445HCID 68591445, compound

Product 1

HCID 68582730HCID 68582730, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
100 °C

Procedure

5-{4-[2-[4-(5-Cyclohex-1-enyl-pyridin-2-yl)-benzyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-1,1-dioxo-2-(2-trimethylsilanyl-ethoxymethyl)-[1,2,5]thiadiazolidin-3-one (40 mg, 0.05 mmol) was dissolved in 1 mL dry acetic acid, iron powder (−325 mesh, 56 mg, 1 mmol) was added and the mixture was then heated at 100° C. under nitrogen for 2 days. At completion, the reaction mixture was then diluted with water/EtOAc and the leftover iron powder was filtered and washed with EtOAc. The combined organic layer was washed with water, saturated NaHCO3 and brine. The organic layer was then dried over Na2SO4, filtered, and the filtrate was concentrated and purified by silica gel chromatography to afford 5-{4-[2-[4-(5-cyclohexyl-pyridin-2-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. filtrationthe leftover iron powder was filtered
  2. washwashed with EtOAc
  3. washThe combined organic layer was washed with water, saturated NaHCO3 and brine
  4. dry with materialThe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-53bf643d5d6348d298ac2996ccdb002f
Source dataset
uspto-grants-2013_03
Patent number
US08404731B2

Reaction notes

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