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

HRID 278942

反応式

HRID 278942 の反応式
[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

参加物

9

反応物 5

HCID 7863AldoximeHCID 31398ChlorosuccinimideHCID 3431191-Cyclopropylprop-2-yn-1-olHCID 57350373N-(2-Chloroethylidene)hydroxylamine3 回HCID 178437389HCID 178437389、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-fdec06412b1b465c9b8f576d496f0246
出典データセット
uspto-grants-2002_03
特許番号
US06362180B1

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