Hydrochloric Acid → HCID 86288167, compound

HRID 633572Notes

Reaction equation

HRID 633572 reaction equation
[F:1][C:2]1[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:6]=1[C:16]1[C:24]2[C:19](=[C:20]([O:45]C)[N:21]=[C:22]([C:25]3[CH:30]=[C:29]([CH2:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:28]=[CH:27][C:26]=3[O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=3[F:44])[CH:23]=2)[N:18]([CH3:47])[CH:17]=1.Cl.O1CCOCC1>>[F:1][C:2]1[CH:51]=[C:50]([F:52])[CH:49]=[CH:48][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12]([CH3:15])(=[O:13])=[O:14])=[CH:7][C:6]=1[C:16]1[C:24]2[CH:23]=[C:22]([C:25]3[CH:30]=[C:29]([CH2:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH:28]=[CH:27][C:26]=3[O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:38]=3[F:44])[NH:21][C:20](=[O:45])[C:19]=2[N:18]([CH3:47])[CH:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90416585HCID 90416585, compound

Product 1

HCID 86288167HCID 86288167, compoundYield 71.6%

Conditions

Temperature
70 °C

Procedure

The product from Example 93A (0.1 g, 0.132 mmol) and 4 M hydrogen chloride in dioxane (5 mL, 20.00 mmol) were combined and heated at 70° C. for 4 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), filtered, and concentrated. Purification by chromatography (0-4% methanol in dichloromethane) afforded the title compound (0.07 g, 71%). %). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.12 (s, 1H) 7.59 (s, 2H) 7.54 (d, J=2.37 Hz, 1H) 7.36-7.50 (m, 4H) 7.17-7.30 (m, 2H) 7.02-7.15 (m, 2H) 6.80 (dd, J=8.31, 1.53 Hz, 2H) 6.74 (s, 1H) 4.48 (s, 2H) 4.46 (s, 2H) 4.12 (s, 3H) 2.93 (s, 3H) 2.91 (s, 3H). MS (ESI+) m/z 741 (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. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (0-4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-68a551af89c94db2a47e57ad6c73cd99
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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