Hydrochloric Acid → HCID 131732305, compound

HRID 1424857Notes

Reaction equation

HRID 1424857 reaction equation
[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[CH:33][C:32]([B:35]4[O:39]C(C)(C)C(C)(C)[O:36]4)=[C:31]([CH2:44][O:45][CH2:46][O:47][CH3:48])[CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([NH:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1.Cl.I([O-])(=O)(=O)=O.[Na+]>CO.O1CCCC1>[CH:1]1([C:4]2[C:5]([N:24]([C:29]3[CH:34]=[CH:33][C:32]([B:35]([OH:36])[OH:39])=[C:31]([CH2:44][O:45][CH2:46][O:47][CH3:48])[CH:30]=3)[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=4)=[C:9]([C:19](=[O:20])[NH:21][CH3:22])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 131732304HCID 131732304, compound

Product 1

HCID 131732305HCID 131732305, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude 5-cyclopropyl-2-(4-fluorophenyl)-6-(N-(3-((methoxymethoxy)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methylsulfonamido)-N-methylbenzofuran-3-carboxamide (215 mg, 0.317 mmol) was dissolved in methanol (1.0 mL) and tetrahydrofuran (4.0 mL). HCl (4.0 mL, 4.00 mmol) was added followed by addition of sodium periodate (542 mg, 2.54 mmol). The mixture was stirred at room temperature overnight. It was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×). The organic phase was washed with 10% aq. Na2S2O3, brine, dried over Na2SO4. Concentrated under reduced pressure, the residue was purified by reversed phase HPLC (10-100 MeCN/H2O with 0.05% TFA) to give product (54 mg, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.47 (q, J=4.36 Hz, 1H) 8.07 (s, 1H) 7.97 (dd, J=8.88, 5.37 Hz, 2H) 7.31-7.53 (m, 5H) 7.14-7.20 (m, 1H) 4.65 (s, 2H) 4.59 (s, 2H) 3.37 (s, 2H) 3.24 (s, 2H) 2.83 (d, J=4.68 Hz, 3H) 2.11-2.26 (m, 1H) 1.01 (br. s., 1H) 0.84 (br. s., 2H) 0.52 (br. s., 1H). LCMS (m/z, ES+)=597 (M+H+).

Workup

  1. customIt 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. concentrationConcentrated under reduced pressure
  6. customthe residue was purified by reversed phase HPLC (10-100 MeCN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-2a64e9895757456ba9f111346586b20a
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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