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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
Notes
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Reaction equation

HRID 633560 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 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

Product 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-oneYield 82%

Conditions

Temperature
70 °C

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-2841c6bbb9e94edb8126c5d9c2df39af
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321764B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes