HCID 59829821, compound → HCID 59829782, compound

HRID 1947177Notes

Reaction equation

HRID 1947177 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[S:37])[NH:16][NH:17][C:18](=O)[C:19]3[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[C:22]([O:28][CH2:29][O:30][CH3:31])=[CH:21][C:20]=3[O:32][CH2:33][O:34][CH3:35])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>[OH-].[Na+]>[CH:25]([C:23]1[C:22]([O:28][CH2:29][O:30][CH3:31])=[CH:21][C:20]([O:32][CH2:33][O:34][CH3:35])=[C:19]([C:18]2[N:14]([C:11]3[CH:12]=[CH:13][C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[CH:9][CH:10]=3)[C:15](=[S:37])[NH:16][N:17]=2)[CH:24]=1)([CH3:27])[CH3:26]

Participants

3

Reactant 1

HCID 59829821HCID 59829821, compound

Product 1

HCID 59829782HCID 59829782, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Crude crystals of 4-[4-(morpholin-4-ylmethyl)-phenyl]-1-(5-isopropyl-2,4-bismethoxymethoxy-benzoyl)thiosemicarbazide (IM5-S-a02) and 5% aqueous sodium hydroxide (30 mL) were placed in a 100 mL eggplant shaped flask and refluxed for 2 hours. After completing the reaction, the reaction mixture was extracted with methylene chloride, and the organic layer was combined, dried over anhydrous sodium sulfate. After filtration and evaporation, the residue thus obtained was purified by silica gel column chromatography to obtain the title compound (IM6-S-a02: 1.43 g, 41.6%).

Workup

  1. temperaturerefluxed for 2 hours
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and evaporation
  6. customthe residue thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36283d6a800d4bf0aa1a45854096f6bf
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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