Hydrochloric Acid → HCID 71263551, compound

HRID 1424813Notes

Reaction equation

HRID 1424813 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:26]=[C:25]([N:27]([C:32]4[CH:37]=[CH:36][C:35]([B:38]5[O:42]C(C)(C)C(C)(C)[O:39]5)=[C:34]([F:47])[CH:33]=4)[S:28]([CH3:31])(=[O:30])=[O:29])[C:24]([CH:48]4[CH2:50][CH2:49]4)=[CH:23][C:17]=3[C:18]=2[C:19]([NH:21][CH3:22])=[O:20])=[CH:10][CH:9]=1.Cl.CCOC(C)=O>C1COCC1.O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:26]=[C:25]([N:27]([C:32]4[CH:37]=[CH:36][C:35]([B:38]([OH:39])[OH:42])=[C:34]([F:47])[CH:33]=4)[S:28]([CH3:31])(=[O:30])=[O:29])[C:24]([CH:48]4[CH2:49][CH2:50]4)=[CH:23][C:17]=3[C:18]=2[C:19](=[O:20])[NH:21][CH3:22])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 89790780HCID 89790780, compound

Product 1

HCID 71263551HCID 71263551, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium periodate (549 mg, 2.57 mmol) was added to a mixture of 2-(4-chlorophenyl)-5-cyclopropyl-6-(N-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methylsulfonamido)-N-methylbenzofuran-3-carboxamide (164 mg, 0.257 mmol) in THF (6 mL) and 1N HCl (3.21 mL, 3.21 mmol). The mixture was stirred at room temperature overnight and EtOAc and water were added. The aqueous layer was extracted with EtOAc (2×) and the combined organic phases were washed with 10% aq. Na2S2O3, brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by reverse phase HPLC (MeCN/H2O with 0.1% TFA) to give the title compound as a white solid (80 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.52 (q, 1H) 8.23 (br. s., 1H) 8.07 (s, 1H) 7.94 (d, 2H) 7.64 (d, 2H) 7.55 (t, 1H) 7.22 (s, 1H) 7.11 (s, 1H) 7.07-7.10 (m, 1H) 3.45 (s, 4H) 2.85 (d, 3H) 2.04-2.15 (m, 1H) 1.00 (br. s., 1H) 0.82 (d, 2H) 0.54 (br. s., 1H). LCMS (m/z, ES+)=557 (M+H+).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (2×)
  2. washthe combined organic phases were washed with 10% aq. Na2S2O3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by reverse phase HPLC (MeCN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-a893e485124d44768498a340468c7148
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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