Mitomycin A → HCID 86737746, compound

HRID 1462478Notes

Reaction equation

HRID 1462478 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[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=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[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=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 310183-Pyridinemethanamine

Product 1

HCID 86737746HCID 86737746, compoundYield 146.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 115 mg mitomycin A (0.33 mmol) in 5 ml of anhydrous methanol, 71 mg 3-aminomethylpyridine (0.66 mmol) was added and the mixture was stirred. The progress of the reaction was checked by TLC and appeared to be complete in 16 hours. The solvent was removed by evaporation under reduced pressure. The residue was chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the column with a mixture of chloroform and ethyl acetate (1:1 by volume) was evaporated to give 107 mg (76% yield) of the desired product as purple-colored crystals having a melting point of 116°-118° after recrystallization from chloroform-hexane and providing the following analysis:

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customThe residue was chromatographed
  3. customThe fraction obtained
  4. washby eluting the column
  5. additionwith a mixture of chloroform and ethyl acetate (1:1 by volume)
  6. customwas evaporated

Sources & evidence

ORD record
ord-c854e745947e4a908ab13f46acd3e421
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

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