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Hydrochloric Acid → HCID 86669401, compound

HRID 337384
Notes
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Reaction equation

HRID 337384 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16](=O)[CH3:17])[C:11]=3[OH:19])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[NH:20]([C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25]1)=[S:23])[NH2:21].Cl.C(OCC)(=O)C>CN(C)C=O>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16](=[N:21][NH:20][C:22]([N:24]4[CH2:29][CH2:28][CH:27]([C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25]4)=[S:23])[CH3:17])[C:11]=3[OH:19])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24855846Methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylateHCID 68161693HCID 68161693, compound

Product 1

HCID 86669401HCID 86669401, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

1-[5-(2,3-dihydro-1H-inden-5-yl)-4-hydroxyl-1-methyl-1H-pyrazol-3-yl]ethanone (50 mg, 0.195 mmol) and methyl 1-(hydrazinecarbonothioyl)piperidine-4-carboxylate (51 mg, 0.234 mmol, synthesized in accordance with WO2006062240) in N,N-dimethylformamide was stirred with concentrated hydrochloric acid (24 μL, 0.293 mmol) at room temperature for 1 day. After the reaction, ethyl acetate was added, and the reaction solution was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride. The resulting organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by medium pressure silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)→ethyl acetate) to obtain the desired product (68 mg, 77% yield).

Workup

  1. additionwas added
  2. washthe reaction solution was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by medium pressure silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)→ethyl acetate)

Sources & evidence

ORD record
ord-0d0593c843124bdab3bf0a9cb962a77b
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889732B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes