Potassium Iodide → HCID 58777598, compound

HRID 1435319Notes

Reaction equation

HRID 1435319 reaction equation
[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

Participants

7

Reactant 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

Product 1

HCID 58777598HCID 58777598, compoundYield 17.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 312751,4-DioxaneSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-c47322391f2940cea7d142fa8a5275e9
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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