Methanol → 9-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

HRID 2212192

Reaction equation

HRID 2212192 reaction equation
[I:1][Si](C)(C)C.COC([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:26])[C:20]=3[C:19]3=[N:27][O:28][C:29]([CH3:30])=[C:18]3[C:17]2=[O:31])[CH2:11]1)=O.CO.C(OCC)C>ClCCl>[IH:1].[Cl:26][C:21]1[C:20]2[C:19]3[C:18](=[C:29]([CH3:30])[O:28][N:27]=3)[C:17](=[O:31])[N:16]([CH:12]3[CH2:13][CH2:14][CH2:15][NH:10][CH2:11]3)[C:25]=2[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 85247Trimethylsilyl iodideHCID 99515613-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid methyl ester

Product 1

HCID 219637129-Chloro-3-methyl-5-piperidin-3-yl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add iodotrimethylsilane (1.87 mL, 13.16 mmol) to a solution of 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1-carboxylic acid methyl ester (2.06 g, 5.48 mmol) in dichloromethane (40 mL). Stir the solution at room temperature under nitrogen overnight. Add methanol (3.2 mL, 78.93 mmol) dropwise, and stir the reaction at room temperature for 30 minutes. Concentrate the reaction, add to diethyl ether, sonicate, and filtere. Dry the solids on a vacuum pump to give 2.36 g of the title compound as a tan solid, 97% yield. 1H NMR: consistent with structure. MS (ion spray) 318 (M+).

Workup

  1. customthe reaction at room temperature for 30 minutes
  2. concentrationConcentrate
  3. customthe reaction
  4. customsonicate
  5. customDry the solids on a vacuum pump

Sources & evidence

ORD record
ord-769fcdf1cdd8433c89c93ffe0bcf8a88
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Linked notes

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