3-Aminopyridine → 1,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(3-pyridylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamate

HRID 2287063Notes

Reaction equation

HRID 2287063 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][C:27]1[CH:28]=[N: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][C:27]3[CH:28]=[N: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 100093-AminopyridineHCID 19972Mitomycin A

Product 1

HCID 867377381,1a,2,8,8a,8b-Hexahydro-8-(hydroxymethyl)-8a-methoxy-5-methyl-6-(3-pyridylamino)-azirino[2',3':3,4]pyrrolo-[1,2-a]indole-4,7-dione carbamateYield 104.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 60 mg mitomycin A (0.17 mmol) in 5 ml of anhydrous methanol was added 61 mg of 3-aminopyridine (1.2 mmol) with stirring. The progress of the reaction was checked periodically by TLC and the reaction appeared to be complete after 44 hours. The solvent was removed by evaporation under reduced pressure and the residue was chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the column with a mixture of ethyl acetate and acetone (10:1 by volume) was evaporated to dryness. Recrystallization from chloroform gave 38 mg (56% yield) of green solid having a melting point of 78°-80° C. 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 ethyl acetate and acetone (10:1 by volume)
  6. customwas evaporated to dryness
  7. customRecrystallization from chloroform

Sources & evidence

ORD record
ord-50435a6f0bc543ab936645fb021d6a90
Source dataset
uspto-grants-1981_05
Patent number
US04268676

Reaction notes

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