Hydrochloric Acid → HCID 135499851, compound

HRID 12275

Reaction equation

HRID 12275 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:11](=[O:33])[N:12](COCC[Si](C)(C)C)[N:13]=[C:14]([C:16]4[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=4)[CH:15]=3)[N:7](COCC[Si](C)(C)C)[C:6]=2[CH:42]=1.FC(F)(F)C(O)=O.[OH-].[Na+].Cl>ClCCl.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:11](=[O:33])[NH:12][N:13]=[C:14]([C:16]4[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=4)[CH:15]=3)[NH:7][C:6]=2[CH:42]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 1363438694-[6-Chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(4-hydroxy-3,5-dimethyl phenyl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one

Product 1

HCID 135499851HCID 135499851, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-[6-Chloro-1-(2-trimethylsilanylethoxymethyl)-1H-benzimidazol-2-yl]-6-(4-hydroxy-3,5-dimethylphenyl)-2-(2-trimethylsilanylethoxymethyl)-2H-pyridazin-3-one is stirred in dichloromethane:trifluoroacetic acid/1:1 at RT for 30 min. The solvent is stripped off in vacuo, and the residue is dissolved in methanol, and 2M sodium hydroxide solution is added. The solution is stirred at RT for 30 min. After the reaction is complete, water is added and 2N hydrochloric acid is used for acidification. The precipitated product is filtered off with suction and purified by column chromatography (RP-HPLC, gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)).

Workup

  1. filtrationThe precipitated product is filtered off with suction
  2. custompurified by column chromatography (RP-HPLC, gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid))

Sources & evidence

ORD record
ord-515db933f0c14a0293ea111721cec9cc
Source dataset
uspto-grants-2010_06
Patent number
US07727989B2

Linked notes

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