Dimethylformamide → 2-[1-(5-Ethyl-pyrimidin-2-yl)-piperidin-4-yl]-5-(2-fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridine

HRID 1471788노트

반응식

HRID 1471788 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[CH:20]=[C:19]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[O:18][C:15]2=[CH:16][N:17]=1.Cl[C:28]1[N:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][N:29]=1.C(N(CC)C(C)C)(C)C.CN(C)C=O>O>[CH2:34]([C:31]1[CH:30]=[N:29][C:28]([N:24]2[CH2:25][CH2:26][CH:21]([C:19]3[O:18][C:15]4=[CH:16][N:17]=[C:12]([C:3]5[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=5[F:1])[CH:13]=[C:14]4[CH:20]=3)[CH2:22][CH2:23]2)=[N:33][CH:32]=1)[CH3:35]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 866945755-(2-Fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine

생성물 1

HCID 717367202-[1-(5-Ethyl-pyrimidin-2-yl)-piperidin-4-yl]-5-(2-fluoro-4-methanesulfonyl-phenyl)-furo[2,3-c]pyridine

시약·촉매·용매 1

HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of 5-(2-fluoro-4-methanesulfonyl-phenyl)-2-piperidin-4-yl-furo[2,3-c]pyridine (70 mg), 2-chloro-5-ethyl-pyrimidine (25 mg), N,N-diisopropyl-ethylamine (67 μL), and N,N-dimethylformamide (1 mL) is stirred at 120° C. for 4 h and then at 100° C. overnight. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to give the title compound. LC (method 1): tR=1.18 min; Mass spectrum (ESI+): m/z=481 [M+H]+.

후처리

  1. customat 100° C.
  2. customovernight
  3. temperatureAfter cooling to room temperature
  4. extractionthe resulting mixture is extracted with ethyl acetate
  5. washThe combined extracts are washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

출처 및 근거

ORD 기록
ord-0bfd503cdfcd4477812882eb938be839
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012456B2

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