Piperidine → HCID 75288717, compound

HRID 383657Notes

Reaction equation

HRID 383657 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([O-:17])=[O:16])=[N:8][C:7]=12)=O.[S:21]1[CH2:27][C:25](=[O:26])[NH:24][C:22]1=[S:23].N1CCCC[CH2:29]1>CCO>[O:26]=[C:25]1[C:27](=[CH:1][C:3]2[CH:4]=[N:5][N:6]3[CH:11]=[CH:10][C:9]([C:12]4[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=4)[C:15]([O:17][CH3:29])=[O:16])=[N:8][C:7]=23)[S:21][C:22](=[S:23])[NH:24]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1201546RhodanineHCID 86649381HCID 86649381, compound

Product 1

HCID 75288717HCID 75288717, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 3-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)benzoate (40 mg, 0.14 mmol) in 0.5 mL EtOH was added rhodanine (19 mg, 0.14 mmol) and piperidine (14 μL, 0.14 mmol). The mixture was stirred at room temperature overnight for three nights. The solid formed was isolated by filtration and purified by preparative TLC (1% MeOH/DCM) to yield methyl 3-(3-((4-oxo-2-thioxothiazolidin-5-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzoate. LCMS (M+1=397)

Workup

  1. customThe solid formed
  2. customwas isolated by filtration
  3. custompurified by preparative TLC (1% MeOH/DCM)

Sources & evidence

ORD record
ord-93950606115543d396b2db86ce0deeb0
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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