HCID 22041814, compound → HCID 86588763, compound

HRID 1791083Notes

Reaction equation

HRID 1791083 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][C:20]([N:26]=[C:27]=[S:28])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Na+].[NH2:30][C:31]1[CH:40]=[C:39]2[C:34]([C:35]([OH:55])=[CH:36][C:37]([S:41]([NH:44][C:45]3[CH:46]=[C:47]([S:51]([O-:54])(=[O:53])=[O:52])[CH:48]=[CH:49][CH:50]=3)(=[O:43])=[O:42])=[CH:38]2)=[CH:33][CH:32]=1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]2[CH:17]=[C:18]3[C:23]([CH:22]=[CH:21][C:20]([NH:26][C:27]([NH:30][C:31]4[CH:40]=[C:39]5[C:34]([C:35]([OH:55])=[CH:36][C:37]([S:41]([NH:44][C:45]6[CH:46]=[C:47]([S:51]([OH:54])(=[O:53])=[O:52])[CH:48]=[CH:49][CH:50]=6)(=[O:42])=[O:43])=[CH:38]5)=[CH:33][CH:32]=4)=[S:28])=[CH:19]3)=[CH:24][CH:25]=2)(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 22041814HCID 22041814, compoundHCID 23390728HCID 23390728, compound

Product 1

HCID 86588763HCID 86588763, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 170 mg (0.39 mmol) of compound 135 dissolved in 5 mL of DMF was added a solution of 100 mg (0.25 mmol) of compound 18 in 5 mL of DMF. The reaction was allowed to stir at ambient temperature. After 4 days, the DMF was removed by rotary evaporation and kept under high vacuum to remove traces of DMF. Then, the resulting residue was treated with dichloromethane (50 mL) and sonicated to form a suspension. The solid, insoluble product was collected by vacuum filtration. This solid was dissolved in methanol and then the methanol was removed by rotary evaporation. The resulting solid was again treated with dichloromethane, sonicated, and collected by vacuum filtration. This provided 172 mg of an orange solid.

Workup

  1. customthe DMF was removed by rotary evaporation
  2. customto remove traces of DMF
  3. additionThen, the resulting residue was treated with dichloromethane (50 mL)
  4. customsonicated
  5. customto form a suspension
  6. filtrationThe solid, insoluble product was collected by vacuum filtration
  7. dissolutionThis solid was dissolved in methanol
  8. customthe methanol was removed by rotary evaporation
  9. additionThe resulting solid was again treated with dichloromethane
  10. customsonicated
  11. filtrationcollected by vacuum filtration

Sources & evidence

ORD record
ord-9254a5d95bdd437794466ad3d5cabb83
Source dataset
uspto-grants-2006_07
Patent number
US07071231B2

Reaction notes

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