Triethylamine → Methyl 1-(6-methoxy-3-(trifluoromethyl)quinolin-2-yl)piperidine-4-carboxylate

HRID 55816

반응식

HRID 55816 반응식
Cl[C:2]1[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:16][CH3:17])[CH:8]=2)[N:3]=1.[CH3:18][O:19][C:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21].CCN(CC)CC>CC(O)C.O>[CH3:17][O:16][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:25]1[CH2:26][CH2:27][CH:22]([C:20]([O:19][CH3:18])=[O:21])[CH2:23][CH2:24]1)[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10]2

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 424914Methyl isonipecotateHCID 866899362-Chloro-6-methoxy-3-(trifluoromethyl)quinoline2회

생성물 1

HCID 66980108Methyl 1-(6-methoxy-3-(trifluoromethyl)quinolin-2-yl)piperidine-4-carboxylate수율 43%

시약·촉매·용매 2

HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

To a solution of 2-chloro-6-methoxy-3-(trifluoromethyl)quinoline (1.00 g, 3.85 mmol) (see Intermediate 6, Step 8 for synthesis) in IPA (5 mL) was added methyl-4-piperidinecarboxylate (5.50 g, 38.5 mmol) and Et3N (1.17 g, 11.6 mmol). The mixture was heated to reflux for 48 hours. The mixture was diluted with water (100 mL) and extracted with DCM (100 mL×3), the combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (PE/EtOAc=15/1) to give the product (600 mg, yield 43%) as a solid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 48 hours
  3. extractionextracted with DCM (100 mL×3)
  4. washthe combined organic layers were washed with brine (200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product, which
  9. customwas purified by column chromatography on silica gel (PE/EtOAc=15/1)

출처 및 근거

ORD 기록
ord-91f426121a724ce7aa13b19804805233
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433618B2

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