Aldoxime → 9-[1-cyclopropyl-1-(3-methyl-isoxazol-5-yl)methyl]-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine

HRID 278942

Reaktionsgleichung

Reaktionsgleichung von HRID 278942
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[C:12]([CH2:18][CH3:19])[NH:13]2.[CH:20]1([CH:23](O)[C:24]#[CH:25])[CH2:22][CH2:21]1.Cl[CH2:28][CH:29]=[N:30][OH:31].C(=NO)C.ClN1C(=O)CCC1=O>C(Cl)Cl.CN(C=O)C.C(N(CC)CC)C>[CH:20]1([CH:23]([N:13]2[C:12]([CH2:18][CH3:19])=[N:11][C:10]3[C:14]2=[N:15][CH:16]=[N:17][C:9]=3[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:24]2[O:31][N:30]=[C:29]([CH3:28])[CH:25]=2)[CH2:22][CH2:21]1

Komponenten

9

Edukt 5

HCID 7863AldoximeHCID 31398ChlorosuccinimideHCID 3431191-Cyclopropylprop-2-yn-1-olHCID 57350373N-(2-Chloroethylidene)hydroxylamine3×HCID 178437389HCID 178437389, Verbindung

Produkt 1

HCID 180013839-[1-cyclopropyl-1-(3-methyl-isoxazol-5-yl)methyl]-6-(2,4-dichlorophenyl)-8-ethyl-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

To a stirring solution of the compound of Example 7241 (90 mg, 0.24 mmol; prepared in a manner similar to that of Example 2 using 6-(2,4-dichlorophenyl)-8-ethyl-9H-purine and 3-cyclopropyl-1-propyn-3-ol) in methylene chloride (2 mL) were added chloroacetaldoxime (25 mg, 0.27 mmol) and triethylamine (0.038 mL, 0.27 mmol). (The chloroacetaldoxime used was previously prepared by reacting equimolar amounts of acetaldoxime and N-chlorosuccinimide in DMF, then extracting the product into diethyl ether and washing with water.) The cycloaddition reaction was monitored by TLC and additional amounts of chloroacetaldoxime and triethylamine were added until all the starting material was consumed. The reaction mixture was purified by adding directly to 4 column packed with silica gel and eluting using a gradient of 100% hexane to 25% ethyl acetate in hexane. 72 mg of a white foam was collected. MS (NH3-CI) 428 (M+H+). HRMS: m/e=428.1037 (M+H+, C21H20Cl2N5O). Purity by reverse phase HPLC>97%.

Aufarbeitung

  1. extractionextracting the product into diethyl ether
  2. washwashing with water
  3. custom) The cycloaddition reaction
  4. additionwere added until all the starting material
  5. customwas consumed
  6. customThe reaction mixture was purified
  7. additionby adding directly to 4 column
  8. washeluting
  9. custom72 mg of a white foam was collected

Quellen und Nachweise

ORD-Eintrag
ord-fdec06412b1b465c9b8f576d496f0246
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362180B1

Verknüpfte Notizen

Wird geladen…