Oxalic Acid → 3,5-diamino-6-chloro-N-2-(2-hydroxy-3-indol-4-yloxy-propylamino)ethyl-pyrazine-2-carboxamide oxalate

HRID 464979Notes

Reaction equation

HRID 464979 reaction equation
[O:1]1[CH:3]([CH2:4][O:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH:8]=[CH:9][NH:10]3)[CH2:2]1.[NH2:15][C:16]1[C:17]([C:24]([NH:26][CH2:27][CH2:28][NH2:29])=[O:25])=[N:18][C:19]([Cl:23])=[C:20]([NH2:22])[N:21]=1.C(O)(C)C.[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36]>CO>[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[NH2:15][C:16]1[C:17]([C:24]([NH:26][CH2:27][CH2:28][NH:29][CH2:2][CH:3]([OH:1])[CH2:4][O:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH:8]=[CH:9][NH:10]3)=[O:25])=[N:18][C:19]([Cl:23])=[C:20]([NH2:22])[N:21]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 3776IsopropanolHCID 6050154-(oxiran-2-ylmethoxy)-1H-indoleHCID 151481293,5-Diamino-N-(2-aminoethyl)-6-chloropyrazine-2-carboxamide

Product 1

HCID 202615703,5-diamino-6-chloro-N-2-(2-hydroxy-3-indol-4-yloxy-propylamino)ethyl-pyrazine-2-carboxamide oxalate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1,2-epoxy-3-(indol-4-yloxy)propane (0.67 g.), 3,5-diamino-6-chloro-N-(2-aminoethyl)pyrazine-2-carboxamide (1.63 g.) and isopropanol (50 ml.) were refluxed together under nitrogen until thin layer chromatography indicated all of the epoxy compound had reacted (about 3 hours). The solvent was removed by rotary evaporator and the resulting yellow solid was chromatographed on silica gel with a 5:1 mixture of chloroform:methanol to give 1.03 g. of product. This material was dissolved in methanol (110 ml.) with warming and the solution was added to oxalic acid (1 equivalent) in methanol (20 ml.). Upon concentration and cooling of the solution, there was obtained 3,5-diamino-6-chloro-N-2-(2-hydroxy-3-indol-4-yloxy-propylamino)ethyl-pyrazine-2-carboxamide oxalate, m.p. 214°-216° C. with decomposition.

Workup

  1. temperaturewere refluxed together under nitrogen until thin layer chromatography
  2. customhad reacted (about 3 hours)
  3. customThe solvent was removed by rotary evaporator
  4. customthe resulting yellow solid was chromatographed on silica gel with a 5:1 mixture of chloroform
  5. custommethanol to give 1.03 g
  6. temperaturewith warming
  7. concentrationUpon concentration
  8. temperaturecooling of the solution

Sources & evidence

ORD record
ord-d733532a0017426abd2033e559aea6c5
Source dataset
uspto-grants-1985_10
Patent number
US04550111

Reaction notes

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