Methanol → 5-(3-Aminocyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

HRID 352235Notes

Reaction equation

HRID 352235 reaction equation
COC(=O)[NH:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([N:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:21])[C:15]=3[C:14]3=[N:22][O:23][C:24]([CH3:25])=[C:13]3[C:12]2=[O:26])[CH2:6]1.C[Si]([I:32])(C)C.CO>ClCCl>[IH:32].[NH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([N:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:21])[C:15]=3[C:14]3=[N:22][O:23][C:24]([CH3:25])=[C:13]3[C:12]2=[O:26])[CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 69848752[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclohexyl]carbamic acid methyl ester

Product 1

HCID 227137135-(3-Aminocyclohexyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one hydroiodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclohexyl]carbamic acid methyl ester, 2.0 g (5.1 mmol) in 50 mL of dichloromethane was added 1.74 mL (12.2 mmol) of trimethylsilyliodide. The reaction mixture was stirred overnight at ambient temperature and was quenched dropwise with 3.0 mL (73.4 mmol) of methanol. The mixture was stirred 30 minutes at ambient temperature and was concentrated to dryness. The residue was triturated with ether, filtered and dried to provide a quantitative yield of the desired isomer as a tan solid. 1H—NMR is consistent with structure. MS (ion spray) 332.1 (M+ for free base).

Workup

  1. stirringThe mixture was stirred 30 minutes at ambient temperature
  2. concentrationwas concentrated to dryness
  3. customThe residue was triturated with ether
  4. filtrationfiltered
  5. customdried
  6. customto provide a quantitative yield of the desired isomer as a tan solid

Sources & evidence

ORD record
ord-52a7a3476d7d420986912451da6dcadf
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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