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

HRID 478332노트

반응식

HRID 478332 반응식
[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(N(CC)CC)C.C(=NO)C.ClN1C(=O)CCC1=O>C(Cl)Cl.CN(C=O)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

참가 물질

9

반응물 6

HCID 7863AldoximeHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 3431191-Cyclopropylprop-2-yn-1-olHCID 57350373N-(2-Chloroethylidene)hydroxylamine2회HCID 178437389HCID 178437389, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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 cyclo addition 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 a 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%.

후처리

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

출처 및 근거

ORD 기록
ord-3a56189179f9431dacfad209eade9a74
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642230B2

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