HCID 59198487, compound → HCID 23581994, compound

HRID 1896534Notes

Reaction equation

HRID 1896534 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]3[C:16]4[C:17]([NH:25]CC5C=CC(OC)=CC=5)=[N:18][CH:19]=[C:20]([C:23]#[N:24])[C:21]=4[S:22][C:12]=3[CH:11]=2)=[CH:4][CH:3]=1.[O:35]([Si](C)(C)C)[K]>C1(C)C=CC=CC=1>[NH2:25][C:17]1[C:16]2[C:13]3[CH:14]=[CH:15][C:10](/[CH:9]=[CH:8]/[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[CH:11][C:12]=3[S:22][C:21]=2[C:20]([C:23]([NH2:24])=[O:35])=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 59198487HCID 59198487, compoundHCID 178504318HCID 178504318, compound

Product 1

HCID 23581994HCID 23581994, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of the product of Step 1 in toluene (0.022 M) was added KOSiMe3 (5 equiv). The mixture was brought to reflux for 30 min, and was then stirred at room temperature overnight. Following removal of solvent under vacuum, the residue was partitioned between EtOAc/THF and H2O. The resulting emulsion was filtered, and the organic layer was dried (MgSO4), filtered, and evaporated. The crude was dissolved in TFA (0.022 M), and the resulting solution was stirred at 45° C. for 1.5 h. After removal of the TFA under vacuum, the crude material was purified by flash chromatography, eluting 1:1 EtOAc:hexanes, EtOAc, and 1:30 MeOH:EtOAc. The product was stirred with 1:10 EtOAc:hexanes containing trace acetone to give the title compound, after filtration, as an off-white solid.

Workup

  1. temperatureto reflux for 30 min
  2. customremoval of solvent under vacuum
  3. customthe residue was partitioned between EtOAc/THF and H2O
  4. filtrationThe resulting emulsion was filtered
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. dissolutionThe crude was dissolved in TFA (0.022 M)
  9. stirringthe resulting solution was stirred at 45° C. for 1.5 h
  10. customAfter removal of the TFA under vacuum
  11. customthe crude material was purified by flash chromatography
  12. washeluting 1:1 EtOAc
  13. stirringThe product was stirred with 1:10 EtOAc

Sources & evidence

ORD record
ord-ca266a7b0b134b4f915c838d9007828e
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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