Potassium Iodide → HCID 58777653、化合物

HRID 1371738ノート

反応式

HRID 1371738 の反応式
[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

参加物

7

反応物 3

HCID 4875Potassium IodideHCID 517044Potassium AcetateHCID 10414333HCID 10414333、化合物

生成物 1

HCID 58777653HCID 58777653、化合物収率 51.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 5234Sodium Chloride溶媒HCID 6228Dimethylformamide溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-1e5871fad24e41c29bdbcfa94c21ef73
出典データセット
uspto-grants-2007_01
特許番号
US07157455B2

反応ノート

読み込み中…