Mitomycin A → HCID 86737748, compound

HRID 1462479Notes

Reaction equation

HRID 1462479 reaction equation
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([O:21][CH3:22])([C@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C:6]=2[C:4](=[O:5])[C:3]=1OC)[C@H:13]1[NH:23][C@H:12]1[CH2:11]3.[NH2:26][CH2:27][C:28]1[S:29][CH:30]=[CH:31][CH:32]=1>CO>[C:18](=[O:17])([OH:19])[NH2:20].[OH:17][CH2:16][CH:15]1[C:6]2[C:4](=[O:5])[C:3]([NH:26][CH2:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)=[C:2]([CH3:1])[C:8](=[O:9])[C:7]=2[N:10]2[CH2:11][CH:12]3[NH:23][CH:13]3[C:14]12[O:21][CH3:22]

Participants

4

Reactant 2

HCID 19972Mitomycin AHCID 34005(2-Thienylmethyl)amine

Product 1

HCID 86737748HCID 86737748, compoundYield 125.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 25 mg mitomycin A (0.071mmol) in 2 ml. of anyhdrous methanol, 16.2 mg 2-aminomethylthiophene (0.143 mmol) was added with stirring. The progress of the reaction was checked periodically by TLC and the reaction appeared to be complete in 24 hours. Removal of the solvent by evaporation under reduced pressure gave a dark-blue residue. The residue was purified by preparative thin-layer chromatography using a pre-coated silica-gel plate (2 mm thickness) and acetone as developing solvent. The product was further purified by recrystallizing from a mixture of chloroform and hexane to give 20 mg (65% yield) of the desired product having a melting point of 92°-94° C. and providing the following analysis:

Workup

  1. customRemoval of the solvent
  2. customby evaporation under reduced pressure
  3. customgave a dark-blue residue
  4. customThe residue was purified by preparative thin-layer chromatography
  5. customThe product was further purified
  6. customby recrystallizing from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-fff1c1ce2e794e31867bcf9018619b57
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

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