HCID 71726538, compound → HCID 71765375, compound

HRID 1400003Notes

Reaction equation

HRID 1400003 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([OH:9])([CH3:8])[CH3:7])[N:3]=[CH:2]1.[CH2:10]([NH:12][C:13]([NH:15][C:16]1[S:17][C:18]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:23][C:22](C3C=NC(C(O)(C)C)=NC=3)=[CH:21][C:19]=2[N:20]=1)=[O:14])[CH3:11]>N1C=CC=CC=1>[CH2:10]([NH:12][C:13]([NH:15][C:16]1[S:17][C:18]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:23][C:22]([N:1]3[CH:5]=[C:4]([C:6]([OH:9])([CH3:8])[CH3:7])[N:3]=[CH:2]3)=[CH:21][C:19]=2[N:20]=1)=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 71726538HCID 71726538, compoundHCID 178458807HCID 178458807, compound

Product 1

HCID 71765375HCID 71765375, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

Compound i (74 mg) and Intermediate 1 (100 mg) were suspended in pyridine with 4 Å mol. sieves. The mixture was degassed and flushed with oxygen and Cu(OAc)2.H2O added. The mixture was again degassed and flushed with oxygen then left stirring at 80° C. for 280 min. The reaction was quenched by adding NH4Cl sat. and diluted with EtOAc and H2O. The mixture was extracted with EtOAc and the organics combined, dried (Na2SO4) and evaporated to dryness. Purification by chromatography on silica, eluting with DCM/MeOH (0-10%) followed by reverse phase chromatography on a C18 column eluting with ACN/H2O afforded Compound 11 (7.5 mg).

Workup

  1. customThe mixture was degassed
  2. customflushed with oxygen and Cu(OAc)2.H2O
  3. additionadded
  4. customThe mixture was again degassed
  5. customflushed with oxygen
  6. waitthen left
  7. customThe reaction was quenched
  8. additionby adding NH4Cl sat.
  9. additiondiluted with EtOAc and H2O
  10. extractionThe mixture was extracted with EtOAc
  11. dry with materialdried (Na2SO4)
  12. customevaporated to dryness
  13. customPurification by chromatography on silica
  14. washeluting with DCM/MeOH (0-10%)
  15. washeluting with ACN/H2O afforded Compound 11 (7.5 mg)

Sources & evidence

ORD record
ord-6f3190afd3d5408a89ccff7e5a2b4fee
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

Loading…