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

HRID 464979ノート

反応式

HRID 464979 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d733532a0017426abd2033e559aea6c5
出典データセット
uspto-grants-1985_10
特許番号
US04550111

反応ノート

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