HCID 20695546, compound → HCID 18365955, compound

HRID 380802Notes

Reaction equation

HRID 380802 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]C(C)(C)C)=[O:30])[C:26](=[O:36])[CH2:25][S:24]1>FC(F)(F)C(O)=O.C(OCC)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: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]([OH:31])=[O:30])[C:26](=[O:36])[CH2:25][S:24]1

Participants

4

Reactant 1

HCID 20695546HCID 20695546, compound

Product 1

HCID 18365955HCID 18365955, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
35 °C

Procedure

A solution of tert-butyl 2-{{2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl}imino}-4-oxo-3-thiazolidineacetate (41.93 g, 76.1 mmol) in trifluoroacetic acid is stirred at room temperature for 3 hours, stirred at 35° C. for 1 hour, and concentrated in vacuc to obtain a yellow liquid. A solution of the yellow liquid in diethyl ether is cooled and filtered to obtain a solid. The solid is washed with diethyl ether and air-dried to give the title product as a white solid (31.6 g) which is identified by 1H and 13C NMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuc
  2. customto obtain a yellow liquid
  3. filtrationfiltered
  4. customto obtain a solid
  5. washThe solid is washed with diethyl ether
  6. customair-dried

Sources & evidence

ORD record
ord-d66faf8a8ec14dd984f287d4ad19ce90
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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