Potassium Iodide → HCID 58777653, compound

HRID 1435317Notes

Reaction equation

HRID 1435317 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]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

Participants

7

Reactant 3

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

Product 1

HCID 58777653HCID 58777653, compoundYield 51.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

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 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

Workup

  1. filtrationSolids were filtered
  2. customcollected
  3. dissolutiondissolved in methylene chloride
  4. washAfter washing with water
  5. customthe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane)
  8. customcrystallized from methylene chloride/ethyl ether

Sources & evidence

ORD record
ord-d4361227662d403ab0961cffc9daacd9
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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