N'-Hydroxycyclopropanecarboximidamide → HCID 19898597, compound

HRID 1196482Notes

Reaction equation

HRID 1196482 reaction equation
[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([OH:17])=O)[CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH:24]1([C:27](=[N:29]O)[NH2:28])[CH2:26][CH2:25]1>C(O)(=O)C>[CH:24]1([C:27]2[N:29]=[C:15]([C:5]3[CH:4]=[C:3]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:2](=[O:1])[N:7]4[C:6]=3[C:11]3[S:12][CH:13]=[CH:14][C:10]=3[CH:9]=[N:8]4)[O:17][N:28]=2)[CH2:26][CH2:25]1.[O:1]=[C:2]1[N:7]2[N:8]=[CH:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[CH:5][CH:4]=[C:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 18957055HCID 18957055, compound

Product 2

HCID 19898597HCID 19898597, compoundHCID 19898603HCID 19898603, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The acid chloride prepared from 2.58 g of 7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine-10-carboxylic acid in accordance with Example 3a) is heated under reflux with 0.8 g of cyclopropanecarboxamide oxime in 50 ml of acetic acid until the reaction is complete. The solvent is removed in vacuo and the residue is chromatographed on silica gel. After recrystallization from ethyl acetate there are obtained 10-(3-cyclopropyl-1,2,4 oxadiazol-5-yl)-7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine as yellow crystals of m.p. 201°-202° and 7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine as yellow crystals of m.p. 242°-244° (acetonitrile).

Workup

  1. temperatureis heated
  2. customThe solvent is removed in vacuo
  3. customthe residue is chromatographed on silica gel
  4. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d0d1ac10388b4d9c80c5aeaa4c6f9263
Source dataset
uspto-grants-1992_05
Patent number
US05114934

Reaction notes

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