HCID 86667098, compound → HCID 86667097, compound

HRID 1184394Notes

Reaction equation

HRID 1184394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:21]3[O:22]C(=O)[CH:24]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[N:25]=3)[CH:12]=[N:13][C:14]=2[O:15][CH2:16][C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:6][C:7]=1[Cl:8]>O.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:14]([O:15][CH2:16][C:17]([F:19])([F:20])[F:18])=[N:13][CH:12]=[C:11]([CH:10]=2)[C:21]([NH:25][CH2:24][C:26](=[O:31])[C:27]([F:29])([F:30])[F:28])=[O:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

HCID 86667098HCID 86667098, compound

Product 1

HCID 86667097HCID 86667097, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 3.00 g 2-[5-(3,4-dichloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-4-(2,2,2-trifluoro-acetyl)-4H-oxazol-5-one in 15 ml water and 15 ml dioxan was heated to reflux for 1 h. The resulting slightly turbid solution was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=9:1 to 1:1. The product fractions were concentrated and the residue was taken up in dichloromethane whereby crystallization occurred. The solid was collected by filtration and washed with little dichloromethane to yield 1.60 g of the title compound as white solid. m.p.: 122-124° C. MS (EI): 474 (M+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. customThe resulting slightly turbid solution was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. customthe organic phase was purified by chromatography on silica gel with heptane
  6. concentrationThe product fractions were concentrated
  7. customwhereby crystallization
  8. filtrationThe solid was collected by filtration
  9. washwashed with little dichloromethane

Sources & evidence

ORD record
ord-05d5e937522e4280b69325b8054a9b1b
Source dataset
uspto-grants-2014_03
Patent number
US08669254B2

Reaction notes

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