Methanol → HCID 18399762, compound

HRID 2184825Notes

Reaction equation

HRID 2184825 reaction equation
BrCC[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[C:26]3[CH:27]=[CH:28][NH:29][C:25]=3[CH:24]=[CH:23][N:22]=2)[CH2:17][CH2:16]1.C([C:49]1[NH:50][CH:51]=[CH:52][N:53]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:54]O>C(#N)C>[N:53]1([CH2:54][C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[NH:9][CH:8]=[C:7]3[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:26]4[CH:27]=[CH:28][NH:29][C:25]=4[CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)[CH:52]=[CH:51][N:50]=[CH:49]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14122587HCID 14122587, compoundHCID 69849125HCID 69849125, compound

Product 1

HCID 18399762HCID 18399762, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3.7 mmol of the compound obtained in Step 6 and 4.1 mmol of tritylimidazole in 50 ml of acetonitrile is heated at reflux for 24 hours and then heated at 60° C. for 24 hours in the presence of 50 ml of methanol. The reaction mixture is then concentrated in vacuo. The residue is taken up in a 5/1 biphasic mixture: dichloromethane/ 20% sodium hydroxide solution. The organic phase is dried, filtered and concentrated under reduced pressure, enabling the expected product to be obtained.

Workup

  1. temperatureat reflux for 24 hours
  2. concentrationThe reaction mixture is then concentrated in vacuo
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto be obtained

Sources & evidence

ORD record
ord-af7bcacca7c142dd9ba3c48f7aa6e7e8
Source dataset
uspto-grants-2002_06
Patent number
US06399616B1

Reaction notes

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