Pyridine → HCID 178511929, compound

HRID 1419244Notes

Reaction equation

HRID 1419244 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([C:14]([OH:16])=[O:15])=[C:9]([OH:17])[CH:8]=[CH:7]2)(=[NH:3])[NH2:2].CS([O-])(=O)=O.N1C=CC=CC=1.Cl.[NH2:30][N:31]=[CH:32][NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>O>[NH2:30][N:31]=[CH:32][NH:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([O:17][C:9]2[CH:8]=[CH:7][C:6]3[C:11](=[CH:12][CH:13]=[C:4]([C:1](=[NH:2])[NH2:3])[CH:5]=3)[C:10]=2[C:14]([OH:16])=[O:15])=[O:39])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 85257MethanesulfonateHCID 136365335HCID 136365335, compoundHCID 178479592HCID 178479592, compound

Product 1

HCID 178511929HCID 178511929, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 930 mg of 6-amidino-1-carboxy-2-naphthol.methanesulfonate were added 10 ml of anhydrous pyridine and then 667.5 mg of 4-aminoiminomethylaminobenzoic acid chloride.hydrochloride, followed by stirring for 2 hours under cooling with ice and then 48 hours under cooling with water. The precipitate was collected by filtration and washed with a small amount of pyridine. To the collected precipitated were added 20 ml of warm DMF and then 0.6 ml of methanesulfonic acid. The resulting solution was added dropwise to 600 ml of ether, followed by stirring for 1 hour under cooling with ice. The supernatant liquid was decanted, and 20 ml of methanol was added to the residue. This solution was added dropwise to 450 ml of acetone, followed by stirring for 15 minutes under cooling with ice. Then, the precipitate was collected by filtration and washed with a small amount of acetone to obtain 869 mg of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with a small amount of pyridine
  4. customTo the collected precipitated
  5. additionwere added 20 ml of warm DMF
  6. additionThe resulting solution was added dropwise to 600 ml of ether
  7. stirringby stirring for 1 hour
  8. temperatureunder cooling with ice
  9. customThe supernatant liquid was decanted
  10. addition20 ml of methanol was added to the residue
  11. additionThis solution was added dropwise to 450 ml of acetone
  12. stirringby stirring for 15 minutes
  13. temperatureunder cooling with ice
  14. filtrationThen, the precipitate was collected by filtration
  15. washwashed with a small amount of acetone

Sources & evidence

ORD record
ord-4e682d7358c748b2bafad717d9d87aca
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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