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

반응식

HRID 2212197 반응식
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

참가 물질

6

반응물 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

생성물 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)-acetamide수율 63.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-fbbecfc0e325409da1c44840f8581115
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

연결된 노트

불러오는 중…