6-Thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one → 4-(1H-Benzimidazol-2-yl)-6-thiophen-3-yl-2H-pyridazin-3-one

HRID 12285

Reaction equation

HRID 12285 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([C:21]3[N:25](COCC[Si](C)(C)C)[C:24]4[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=4[N:22]=3)[C:9](=[O:20])[N:10](COCC[Si](C)(C)C)[N:11]=2)=[CH:2]1>ClCCl.FC(F)(F)C(O)=O.C(S)(S)C>[NH:25]1[C:24]2[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=2[N:22]=[C:21]1[C:8]1[C:9](=[O:20])[NH:10][N:11]=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH:7]=1

Participants

5

Reactant 1

HCID 686802276-Thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

Product 1

HCID 1359787884-(1H-Benzimidazol-2-yl)-6-thiophen-3-yl-2H-pyridazin-3-one

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 336451,1-EthanedithiolSolvent

Procedure

30 mg of 6-thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl -ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one is dissolved in a mixture of dichloromethane (1 ml) and trifluoroacetic acid (1 ml), 18 μl of ethanedithiol are added, and the resulting solution is stirred at room temperature for 18 hours. After the solvent has been distilled off, the crude product is purified by preparative RP-HPLC (0-100% acetonitrile (+0.05% formic acid) in water (+0.05% formic acid)).

Workup

  1. additionare added
  2. distillationAfter the solvent has been distilled off
  3. customthe crude product is purified by preparative RP-HPLC (0-100% acetonitrile (+0.05% formic acid) in water (+0.05% formic acid))

Sources & evidence

ORD record
ord-a0bb0e36af1c4605afc2d9a01c94eb29
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Linked notes

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