Potassium Iodide → HCID 58777598, 화합물

HRID 1371740노트

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HRID 1371740 반응식
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31]Cl)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1.[I-].[K+].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>O1CCOCC1.O.[Cl-].[Na+]>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1

참가 물질

7

반응물 3

HCID 4875Potassium IodideHCID 8083MorpholineHCID 10458099[4-Amino-2-[1-(3-chloro-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone

생성물 1

HCID 58777598HCID 58777598, 화합물수율 17.5%

시약·촉매·용매 3

HCID 962Water용매HCID 5234Sodium Chloride용매HCID 312751,4-Dioxane용매

실험 절차

A suspension of [4-amino-2-[1-(3-chloro-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone (80 mg, 0.16 mmol, Example 272), potassium iodide (200 mg, 1.2 mmol), morpholine (200 mg, 4.3 mmol) in dioxane (12 mL) was heated at reflux under nitrogen for 48 hours. The resulting solution was diluted with 20 mL of cold water plus 20 mL of saturated aqueous sodium chloride. Solids were filtered and dissolved in methylene chloride. The organic layer was separated and dried (Na2SO4). The residue was purified by silica gel chromatography (triethylamine/methanol/methylene chloride 1:10:90) and crystallized from methylene chloride/hexane to give [4-amino-2-[1-(3-morpholin-4-yl-propane-1-sulfonyl)-piperidin-4-ylamino]-pyrimidin-5-yl]-(5-fluoro-2-methoxy-phenyl)-methanone as a white solid (15 mg, 17% yield). HRMS, observed: 537.2296; Calcd for (M+H)+: 537.2290

후처리

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 48 hours
  3. filtrationSolids were filtered
  4. dissolutiondissolved in methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customThe residue was purified by silica gel chromatography (triethylamine/methanol/methylene chloride 1:10:90)
  8. customcrystallized from methylene chloride/hexane

출처 및 근거

ORD 기록
ord-02c465224b3d45809294adf2cec227ed
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157455B2

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