Cyclopropylamine → HCID 19838050, compound

HRID 2287062Notes

Reaction equation

HRID 2287062 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.[CH:27]1([NH2:30])[CH2:29][CH2:28]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:30][CH:27]3[CH2:29][CH2:28]3)=[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 69828CyclopropylamineHCID 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 19838050HCID 19838050, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 75 mg (0.2 mmol) of N-methylmitomycin A in 10 ml of anhydrous methanol, 2 ml of cyclopropylamine was added with stirring. The reaction mixture was stirred overnight, whereupon TLC indicated no remaining 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 column with ethyl acetate was evaporated under reduced pressure. Recrystallization from a mixture of methylene chloride and hexane gave 47.8 mg (59.7% yield) of the desired product as purple-colored crystals having a melting point of 166°-167° (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 column with ethyl acetate
  6. customwas evaporated under reduced pressure
  7. customRecrystallization
  8. additionfrom a mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-012fbdd0e7f748a98e6338ce594f3434
Source dataset
uspto-grants-1981_05
Patent number
US04268676

Reaction notes

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