Potassium Iodide → HCID 58777653, 화합물

HRID 1371738노트

반응식

HRID 1371738 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]N3CCCC3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)[N:3]=1.[I-].[K+].[C:39]([O-:42])(=[O:41])[CH3:40].[K+]>CN(C)C=O.O.[Cl-].[Na+]>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[CH:6][N:5]=[C:4]([NH:19][CH:20]2[CH2:21][CH2:22][N:23]([S:26]([CH2:29][CH2:30][CH2:31][O:42][C:39](=[O:41])[CH3:40])(=[O:28])=[O:27])[CH2:24][CH2:25]2)[N:3]=1

참가 물질

7

반응물 3

HCID 4875Potassium IodideHCID 517044Potassium AcetateHCID 10414333HCID 10414333, 화합물

생성물 1

HCID 58777653HCID 58777653, 화합물수율 51.5%

시약·촉매·용매 3

HCID 962Water용매HCID 5234Sodium Chloride용매HCID 6228Dimethylformamide용매

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 273), potassium iodide (100 mg, 0.61 mmol), and potassium acetate (120 mg, 1.22 mmol) in dimethylformamide (6 mL) was heated at 65–85° C. under nitrogen for 14 hours. The resulting solution was diluted with 50 mL of cold water plus 20 mL of saturated aqueous sodium chloride. Solids were filtered, collected and dissolved in methylene chloride. After washing with water, the organic layer was separated and dried (Na2SO4). The residue was purified by silica gel chromatography (ethyl acetate/hexane) and crystallized from methylene chloride/ethyl ether to give acetic acid 3-[4-[4-amino-5-(5-fluoro-2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-sulfonyl]-propyl ester as a white solid (42 mg, 51% yield). HRMS, observed: 510.1822; Calcd for (M+H)+: 510.1817

후처리

  1. temperaturewas heated at 65–85° C. under nitrogen for 14 hours
  2. filtrationSolids were filtered
  3. customcollected
  4. dissolutiondissolved in methylene chloride
  5. washAfter washing with water
  6. customthe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane)
  9. customcrystallized from methylene chloride/ethyl ether

출처 및 근거

ORD 기록
ord-1e5871fad24e41c29bdbcfa94c21ef73
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157455B2

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