Allylamine → HCID 88715263, compound

HRID 1462469Notes

Reaction equation

HRID 1462469 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])[CH:28]=[CH2:29]>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][CH:28]=[CH2:29])=[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 7853AllylamineHCID 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 carbonimidate

Product 1

HCID 88715263HCID 88715263, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 100 mg (0.275 mmol) of N-methylmitomycin A in 15 ml of anhydrous methanol, 58 mg (1 mmol) of allylamine was added with stirring. The reaction mixture was stirred overnight, whereupon TLC indicated the absence of starting material. The solvent was then evaporated under reduced pressure and the residue was chromatographed using silica-gel as adsorbent. The fraction obtained by eluting the colum with ethyl acetate was evaporated to dryness. Recrystallization from a mixture of ethyl acetate and hexane gave 38.5 mg (38% yield) of the desired product as purple-colored crystals having a melting point of 70°-71° C. (decomposing) and providing the following analysis:

Workup

  1. stirringThe reaction mixture was stirred overnight, whereupon TLC
  2. customThe solvent was then evaporated under reduced pressure
  3. customthe residue was chromatographed
  4. customThe fraction obtained
  5. washby eluting the colum with ethyl acetate
  6. customwas evaporated to dryness
  7. customRecrystallization
  8. additionfrom a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-2c617a0e7882480bb7a48bf2b1d96d24
Source dataset
uspto-grants-1984_07
Patent number
US04460599

Reaction notes

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