Ethylenediamine → HCID 178521322, compound

HRID 365217Notes

Reaction equation

HRID 365217 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.NCCNN1[C:21]23[C:25](=[CH:26][CH:27]=[CH:28][C:20]2=CN=C1)[NH:24][CH:23]=[CH:22]3.Cl[N:30]1C2=NC3C(C2=C[N:32]=[CH:31]1)=CC=CC=3.[CH2:43]([NH2:46])[CH2:44][NH2:45].C(O)(=O)/C=C/C(O)=O>C(OCC)(=O)C.C(O)C.CN(C)C=O>[O:5]([CH2:1][CH:2]([OH:4])[CH2:3][NH:45][CH2:44][CH2:43][NH:46][C:20]1[C:28]2=[N:30][CH:31]=[N:32][C:26](=[CH:27]2)[C:25]2[C:21]=1[CH:22]=[CH:23][N:24]=2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 3301EthylenediamineHCID 31217Phenyl glycidyl etherHCID 444972Fumaric AcidHCID 20237821HCID 20237821, compoundHCID 20237851HCID 20237851, compound

Product 1

HCID 178521322HCID 178521322, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584252Ethanol ethylacetateSolvent

Conditions

Temperature
50 °C

Procedure

1.22 g. phenyl glycidyl ether and 3.7 g. 1-(2-aminoethylamino)-pyrimido[4,5-d]indole (prepared by reacting 1-chloropyrimido[4,5-b]indole with an excess of ethylenediamine) are stirred for 7 hours at 50° C. in 20 ml. dimethylformamide. The reaction mixture is then evaporated and the residue is purified chromatographically over a silica gel column using, as elution agent, methylene chloride-methanol-triethylamine (10:2:0.3 v/v/v). The residue obtained by evaporation of the pure fraction is mixed in ethyl acetate-ethanol with fumaric acid and the product obtained is recrystallized from ethanol. There is obtained 0.3 g. (15% of theory) of colorless crystals: m.p. 187°-188° C.

Workup

  1. customThe reaction mixture is then evaporated
  2. customthe residue is purified chromatographically over a silica gel column
  3. washusing, as elution agent, methylene chloride-methanol-triethylamine (10:2:0.3 v/v/v)
  4. customThe residue obtained by evaporation of the pure fraction
  5. customthe product obtained
  6. customis recrystallized from ethanol
  7. customThere is obtained 0.3 g

Sources & evidence

ORD record
ord-5c50464d892843c7a6a2a141418ad63a
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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