Potassium Iodide → 2-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-N-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 2212197

Reaction equation

HRID 2212197 reaction equation
I.[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1.Br[CH2:25][C:26]([NH:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=1)=[O:27].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:2][C:3]1[C:4]2[C:5]3[C:6](=[C:20]([CH3:23])[O:21][N:22]=3)[C:7](=[O:19])[N:8]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:25][C:26]([NH:28][C:29]4[CH:30]=[C:31]([O:39][CH3:40])[C:32]([O:37][CH3:38])=[C:33]([O:35][CH3:36])[CH:34]=4)=[O:27])[CH2:14]3)[C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 219637112-Bromo-N-(3,4,5-trimethoxy-phenyl)-acetamideHCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Product 1

HCID 219637142-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-N-(3,4,5-trimethoxy-phenyl)-acetamideYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 9-chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide (50 mg, 0.11 mmol), 2-bromo-N-(3,4,5-trimethoxy-phenyl)-acetamide (38 mg, 0.12 mmol), and tetrahydrofuran (3 mL) to a roundbottom flask. Stir and add potassium iodide (2 mg, 0.01 mmol) and potassium carbonate (34 mg, 0.25 mmol) at room temperature under nitrogen overnight. Concentrate the reaction, partitions between water and 20% isopropanol/chloroform, and separate. Was the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 37.6 mg of the title compound as an orange solid, 62% yield. 1H NMR: consistent with structure. MS (ion spray) 541 (M+).

Workup

  1. concentrationConcentrate
  2. customthe reaction, partitions between water and 20% isopropanol/chloroform
  3. customseparate
  4. dry with materialdry over magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform)

Sources & evidence

ORD record
ord-fbbecfc0e325409da1c44840f8581115
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Linked notes

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