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Hydrochloric Acid → 3-{2-(2,4-difluorophenoxy)-5-[(methylsulfonyl)methyl]pyridin-3-yl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 633560
ノート
印刷プレビュー

反応式

HRID 633560 の反応式
[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[C:10]([C:11]2[C:19]3[C:14](=[C:15]([O:20]C)[N:16]=[CH:17][CH:18]=3)[N:13]([CH3:22])[CH:12]=2)=[CH:9][C:8]([CH2:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:7][N:6]=1.Cl.O1CCOCC1>>[F:1][C:2]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[C:10]([C:11]2[C:19]3[CH:18]=[CH:17][NH:16][C:15](=[O:20])[C:14]=3[N:13]([CH3:22])[CH:12]=2)=[CH:9][C:8]([CH2:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:7][N:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 904160973-(2-(2,4-difluorophenoxy)-5-(methylsulfonylmethyl)pyridin-3-yl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

生成物 1

HCID 904170183-{2-(2,4-difluorophenoxy)-5-[(methylsulfonyl)methyl]pyridin-3-yl}-1-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one収率 82%

反応条件

温度
70 °C

実験手順

The product from Example 60F (0.097 g, 0.211 mmol) and 4 M hydrogen chloride in dioxane (5 mL, 20.00 mmol) were combined and heated at 70° C. for 18 hours, cooled and concentrated. The residue was partitioned between ethyl acetate and water adjusting the pH to 7. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), treated with 3-mercaptopropyl functionalized silica gel, filtered, and concentrated. Purification by trituration (1:1 dichloromethane/heptane) afforded the title compound (0.077 g, 82%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.03 (d, J=5.43 Hz, 1H) 8.02 (d, J=2.37 Hz, 1H) 7.95 (d, J=2.37 Hz, 1H) 7.75 (s, 1H) 7.39-7.50 (m, 2H) 7.10-7.19 (m, 1H) 6.93-6.97 (m, 1H) 6.66 (d, J=6.44 Hz, 1H) 4.57 (s, 2H) 4.14 (s, 3H) 2.98 (s, 3H). MS (ESI+) m/z 446 (M+H)+.

後処理

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water adjusting the pH to 7
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous Na2SO4)
  6. additiontreated with 3-mercaptopropyl functionalized silica gel
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by trituration (1:1 dichloromethane/heptane)

出典と根拠

ORDレコード
ord-2841c6bbb9e94edb8126c5d9c2df39af
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321764B2

反応ノート

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