Triethylamine → Benzyl [(3S)-1-(3-bromo-5-nitropyridin-4-yl)piperidin-3-yl]carbamate

HRID 924437노트

반응식

HRID 924437 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1Cl.[NH:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1.C(N(CC)CC)C>C(O)(C)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13]1

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 1514175Benzyl (3S)-piperidin-3-ylcarbamateHCID 125100523-Bromo-4-chloro-5-nitropyridine

생성물 1

HCID 86726888Benzyl [(3S)-1-(3-bromo-5-nitropyridin-4-yl)piperidin-3-yl]carbamate수율 91.9%

시약·촉매·용매 3

HCID 962Water용매HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-bromo-4-chloro-5-nitropyridine (from Ark Pharm, 0.050 g, 0.21 mmol), benzyl (3S)-piperidin-3-ylcarbamate (0.059 g, 0.25 mmol), and triethylamine (0.088 mL, 0.63 mmol) in isopropyl alcohol (0.8 mL) was heated at 90° C. in a sealed vial for 16 h. The reaction mixture was diluted with EtOAc (40 mL) and water (3 mL). The layers were separated and the organic layer was washed with water (3×3 mL) and the combined aqueous phases were extracted with EtOAc (3 mL). The combined organic layers were washed with brine (3 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the sub-title compound (0.084 g). The crude product was used without further purification in the subsequent reaction. LCMS (ESI) calc. for C18H20BrN4O4[M+H]+: m/z=435.1. found 435.0/437.0.

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed with water (3×3 mL)
  3. extractionthe combined aqueous phases were extracted with EtOAc (3 mL)
  4. washThe combined organic layers were washed with brine (3 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-99ea7291633e465eb1d7b9e2ad710623
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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