Potassium Carbonate → (S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1047159노트

반응식

HRID 1047159 반응식
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[N:11][CH:12]=1)[N:9]([C@H:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24].C([O-])([O-])=O.[K+].[K+].Cl.Br[CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>C(#N)C>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[N:11][CH:12]=1)[N:9]([C@H:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH2:14]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 129555404-(2-Bromoethyl)morpholine hydrochlorideHCID 86665046(S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate hydrochloride

생성물 1

HCID 69621275(S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

(S)-ethyl 6-bromo-4-oxo-1-(piperidin-3-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylate hydrochloride Intermediate 33, 0.400 g, 0.96 mmol) and K2CO3 (0.663 g, 4.80 mmol) were taken up in acetonitrile (3 mL) and 4-(2-bromoethyl)morpholine hydrochloride (0.221 g, 0.96 mmol) added. The reaction mixture was heated to 120° C. in the microwave for 30 min. The reaction mixture was cooled to room temperature and filtered, and the inorganics were washed with EtOAc two times. The solvent was removed in vacuo. (S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.420 g, 89%) was recovered as a tan solid and will be carried on without further purification. MS (ES)(M+H)+: 494 for C22H29BrN4O4.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washthe inorganics were washed with EtOAc two times
  4. customThe solvent was removed in vacuo
  5. custom(S)-ethyl 6-bromo-1-(1-(2-morpholinoethyl)piperidin-3-yl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (0.420 g, 89%) was recovered as a tan solid
  6. customwill be carried on without further purification

출처 및 근거

ORD 기록
ord-a05205c87013454993e89832e700d999
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569484B2

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