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

HRID 352235노트

반응식

HRID 352235 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-52a7a3476d7d420986912451da6dcadf
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743794B2

반응 노트

불러오는 중…