Acetic Acid → HCID 20695533, compound

HRID 380801Notes

Reaction equation

HRID 380801 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[N:22]=[C:23]1[N:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26](=[O:34])[CH2:25][S:24]1.[CH3:35][C:36]([CH3:38])=O.N1CCCCC1.C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[N:22]=[C:23]1[N:27]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26](=[O:34])[C:25](=[C:36]([CH3:38])[CH3:35])[S:24]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180Acetone2×HCID 8082PiperidineHCID 20695526HCID 20695526, compound

Product 1

HCID 20695533HCID 20695533, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate (2.0 g, 3.83 mmol), acetone (0.562 mL, 7.65 mmol), piperidine (0.20 mL, 2.02 mmol) and acetic acid (20 μL) in ethanol is refluxed for 90 minutes, treated with additional acetone (0.562 mL), refluxed for 3.5 hours, stirred at room temperature overnight, concentrated in vacuo, and chased with ethyl acetate to obtain a residue. Column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:3) gives the title product as a white solid (1.5 g, mp 67-80° C.).

Workup

  1. temperatureis refluxed for 90 minutes
  2. temperaturerefluxed for 3.5 hours
  3. concentrationconcentrated in vacuo
  4. customchased with ethyl acetate to obtain a residue

Sources & evidence

ORD record
ord-11b5cb7312a74753ac5d89fd3f643e72
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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