Hydrochloric Acid → HCID 71263627, compound

HRID 1424829Notes

Reaction equation

HRID 1424829 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:18]([C:23]2[C:42]([CH:43]3[CH2:45][CH2:44]3)=[CH:41][C:26]3[C:27]([C:37]([NH:39][CH3:40])=[O:38])=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)[O:29][C:25]=3[CH:24]=2)[S:19]([CH3:22])(=[O:21])=[O:20])[CH:6]=[CH:7][C:8]=1[B:9]1[O:13]C(C)(C)C(C)(C)[O:10]1)#[N:2].Cl.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([N:18]([C:23]2[C:42]([CH:43]3[CH2:44][CH2:45]3)=[CH:41][C:26]3[C:27]([C:37](=[O:38])[NH:39][CH3:40])=[C:28]([C:30]4[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=4)[O:29][C:25]=3[CH:24]=2)[S:19]([CH3:22])(=[O:21])=[O:20])[CH:6]=[CH:7][C:8]=1[B:9]([OH:10])[OH:13])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 131732288HCID 131732288, compound

Product 1

HCID 71263627HCID 71263627, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 6-(N-(3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (108 mg, 0.172 mmol) was dissolved in tetrahydrofuran (4.0 mL). 1M HCl (2.059 mL, 1.029 mmol) was added followed by sodium periodate (294 mg, 1.373 mmol). The mixture was stirred at room temperature overnight. The reaction was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×). The organic phase was washed with 10% aq. Na2S2O3, brine, and dried over Na2SO4. After concentration, the crude residue was purified by reverse phase HPLC (10-100% MeCN/H2O with 0.1% TFA) to give the title compound as a white solid (58 mg, 62%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.60 (br. s., 1H) 8.48 (q, 1H) 8.12 (s, 1H) 7.94-8.02 (m, 2H) 7.73-7.80 (m, 2H) 7.58-7.65 (m, 1H) 7.41 (t, 2H) 7.21 (s, 1H) 3.46 (s, 3H) 2.84 (d, 3H) 2.03-2.14 (m, 1H) 0.99 (br. s., 1H) 0.85 (br. s., 2H) 0.45 (br. s., 1H). LCMS (m/z, ES+)=548 (M+H+).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. washThe organic phase was washed with 10% aq. Na2S2O3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. customthe crude residue was purified by reverse phase HPLC (10-100% MeCN/H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-2ec54d39aaea496c9fae7dceeaf6cc77
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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