(6,8a-Dimethoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl hydrogen carbonimidate → HCID 88629575, compound

HRID 2287068Notes

Reaction equation

HRID 2287068 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[N:23]([CH3:24])[C@H:12]1[CH2:11]3.[CH2:27]([NH2:30])[C:28]#[CH:29]>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:30][CH2:27][C:28]#[CH:29])=[C:2]([CH3:1])[C:8](=[O:9])[C:7]=2[N:10]2[CH2:11][CH:12]3[N:23]([CH3:24])[CH:13]3[C:14]12[O:21][CH3:22]

Participants

4

Reactant 2

HCID 159845(6,8a-Dimethoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazireno[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl hydrogen carbonimidateHCID 239041Propargylamine

Product 1

HCID 88629575HCID 88629575, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 107 mg (0.27 mmol) of N-methylmitomycin A in 10 ml of anhydrous methanol was stirred with 85 mg (1.5 mmol) of propargylamine for 3 hours, whereupon TLC indicated no remaining starting material. 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 ethyl acetate was evaporated under reduced pressure. Recrystallization from a mixture of methylene chloride and hexane gave 52.2 mg (50% yield) of the desired product as purple-colored crystals having a melting point of 86°-87° (decomposing) 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 with ethyl acetate
  5. customwas evaporated under reduced pressure
  6. customRecrystallization
  7. additionfrom a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-dfb692a3d0184adab1d992f31d2c942b
Source dataset
uspto-grants-1981_05
Patent number
US04268676

Reaction notes

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