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

HRID 1471788ノート

反応式

HRID 1471788 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-0bfd503cdfcd4477812882eb938be839
出典データセット
uspto-grants-2015_04
特許番号
US09012456B2

反応ノート

読み込み中…