HCID 68881564, compound → HCID 66725376, compound

HRID 1888802Notes

Reaction equation

HRID 1888802 reaction equation
[CH3:1][S:2]([C:5]1[CH:41]=[CH:40][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:39])[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)[C:16]([CH3:28])=[C:17]([C:19]([N:21](C(=O)C(C)C)[NH2:22])=O)[CH:18]=2)=[O:12])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14](=[O:39])[N:15]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=3)[C:16]([CH3:28])=[C:17]([C:19]3[O:12][C:11]([CH:13]([CH3:14])[CH3:18])=[N:22][N:21]=3)[CH:18]=2)=[O:12])=[CH:40][CH:41]=1)(=[O:4])=[O:3]

Participants

3

Reactant 1

HCID 68881564HCID 68881564, compound

Product 1

HCID 66725376HCID 66725376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

The compound obtained in step (b) (0.02 g, 0.034 mmol) in TMS-polyphosphate (3 ml, PPSE in DCM, Synthesis 1982, page 591-592) was stirred in a sealed vial and heated at 70° C. for 3 h. LC-MS showed complete conversion of the linear starting material to a compound with the expected MW. The cooled solution was diluted with DCM (10 ml) and was washed with water (10 ml). The organic phase was collected and the aqueous phase was extracted with another portion of DCM (10 ml). The combined organic phase was washed with brine and was then dried with Na2SO4. Filtration and evaporation of the solution gave a white solid. Purification of this material by preparative HPLC provided pure fractions which were freeze-dried. The title compound was obtained as a white solid (0.015 g, 77%).

Workup

  1. washwas washed with water (10 ml)
  2. customThe organic phase was collected
  3. extractionthe aqueous phase was extracted with another portion of DCM (10 ml)
  4. washThe combined organic phase was washed with brine
  5. dry with materialwas then dried with Na2SO4
  6. filtrationFiltration and evaporation of the solution
  7. customgave a white solid
  8. customPurification of this material by preparative HPLC
  9. customprovided pure fractions which
  10. customwere freeze-dried

Sources & evidence

ORD record
ord-5582ff9a0be7418284cb286e2ccae1e5
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

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