Hydrochloric Acid → HCID 90416369, compound

HRID 633567Notes

Reaction equation

HRID 633567 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12]([C:13]3[CH:18]=[C:17]([CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:16]=[CH:15][C:14]=3[O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[CH:11][N:10]([CH3:33])[C:5]2=[C:6]([O:8]C)[N:7]=1.[ClH:34].O1CCOCC1>>[Cl:34][C:2]1[NH:7][C:6](=[O:8])[C:5]2[N:10]([CH3:33])[CH:11]=[C:12]([C:13]3[CH:18]=[C:17]([CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:16]=[CH:15][C:14]=3[O:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90416822HCID 90416822, compound

Product 1

HCID 90416369HCID 90416369, compoundYield 74%

Conditions

Temperature
70 °C

Procedure

The product from Example 91E (0.064 g, 0.119 mmol) and 4 M hydrogen chloride in dioxane (2 mL, 8.00 mmol) were combined and heated at 70° C. for 2 hours, cooled and concentrated. Purification by trituration (1:1 dichloromethane/heptane) afforded the title compound (0.042 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.91 (s, 1H) 7.60 (s, 1H) 7.57 (d, J=2.03 Hz, 1H) 7.43-7.52 (m, 1H) 7.19-7.30 (m, 2H) 7.05-7.15 (m, 1H) 6.82 (d, J=8.14 Hz, 1H) 6.68 (s, 1H) 4.53 (s, 2H) 4.07 (s, 3H) 2.94 (s, 3H). MS (ESI+) m/z 479 (M+H)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customPurification by trituration (1:1 dichloromethane/heptane)

Sources & evidence

ORD record
ord-46aa6c9580834a8f8aca50e0b7714e99
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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