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

HRID 352235ノート

反応式

HRID 352235 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-52a7a3476d7d420986912451da6dcadf
出典データセット
uspto-grants-2004_06
特許番号
US06743794B2

反応ノート

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