Hydrochloric Acid → HCID 71263591, compound

HRID 2272357Notes

Reaction equation

HRID 2272357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([C:26]4[CH:31]=[CH:30][C:29]([B:32]5[O:36]C(C)(C)C(C)(C)[O:33]5)=[C:28]([C:41]#[N:42])[CH:27]=4)[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([CH:43]4[CH2:45][CH2:44]4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.Cl.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([C:26]4[CH:31]=[CH:30][C:29]([B:32]([OH:36])[OH:33])=[C:28]([C:41]#[N:42])[CH:27]=4)[S:22]([CH3:25])(=[O:23])=[O:24])[C:18]([CH:43]4[CH2:44][CH2:45]4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:14])[NH:15][CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 131732308HCID 131732308, compound

Product 1

HCID 71263591HCID 71263591, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 2-(4-chlorophenyl)-6-(N-(3-cyano-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methylsulfonamido)-5-cyclopropyl-N-methylbenzofuran-3-carboxamide (162 mg, 0.251 mmol) was dissolved in tetrahydrofuran (6.0 mL). HCl (3.01 mL, 1.505 mmol) was added followed by addition of sodium periodate (429 mg, 2.006 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 and 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 (88 mg, 62%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.54-8.74 (br.s., 1H) 8.51 (q, J=4.49 Hz, 2H) 8.13 (s, 1H) 7.93 (d, J=8.78 Hz, 2H) 7.74-7.79 (m, 2H) 7.58-7.67 (m, 3H) 7.22 (s, 1H) 3.47 (s, 3H) 2.84 (d, J=4.68 Hz, 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+)=564 (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 and 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-2b50d28a6e874a6babae04281ae60d2f
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

Loading…