Hydrochloric Acid → HCID 71607776, compound

HRID 2272373Notes

Reaction equation

HRID 2272373 reaction equation
I([O-])(=O)(=O)=O.[Na+].Cl.[CH:8]1([C:11]2[C:12]([N:31]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][CH2:43][B:44]4[O:48]C(C)(C)C(C)(C)[O:45]4)[CH:37]=3)[S:32]([CH3:35])(=[O:34])=[O:33])=[CH:13][C:14]3[O:18][C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)=[C:16]([C:26]([NH:28][CH3:29])=[O:27])[C:15]=3[CH:30]=2)[CH2:10][CH2:9]1>C1COCC1.CCOC(C)=O>[CH:8]1([C:11]2[C:12]([N:31]([C:36]3[CH:37]=[C:38]([CH:39]=[CH:40][CH:41]=3)[CH2:42][CH2:43][B:44]([OH:48])[OH:45])[S:32]([CH3:35])(=[O:33])=[O:34])=[CH:13][C:14]3[O:18][C:17]([C:19]4[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=4)=[C:16]([C:26](=[O:27])[NH:28][CH3:29])[C:15]=3[CH:30]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 131732325HCID 131732325, compound

Product 1

HCID 71607776HCID 71607776, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium periodate (380 mg, 1.78 mmol) and 1N aqueous HCl (1.5 mL, 1.5 mmol) were added to a cold (0° C.) solution of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)phenyl)methylsulfonamido)benzofuran-3-carboxamide (75 mg, 0.119 mmol) in THF (3 mL). The mixture was stirred at 0° C. for 10 min then warmed to room temperature. After one hour, the reaction mixture was diluted with EtOAc and the organic layer was separated and washed with 5% aqueous sodium thiosulfate and brine and dried over sodium sulfate. The solvent was evaporated and the residue was subjected to reverse phase HPLC (C18, acetonitrile:water with 0.1% formic acid) to give the title compound (22 mg, 34%) as a white powder. 1H NMR (400 MHz, DMSO-d6) d ppm 8.42-8.53 (m, 1H) 8.06-8.13 (m, 1H) 7.92-8.02 (m, 2H) 7.55 (s, 2H) 7.34-7.46 (m, 3H) 7.24-7.30 (m, 2H) 7.14-7.18 (m, 1H) 7.04-7.11 (m, 1H) 2.83 (d, J=4.68 Hz, 3H) 2.58-2.67 (m, 2H) 2.48-2.55 (m, 3H) 2.15-2.31 (m, 1H) 0.94-1.11 (m, 1H) 0.75-0.94 (m, 4H) 0.47 (m, 1H). LCMS (m/z, ES+)=551 (M+H+).

Workup

  1. temperaturethen warmed to room temperature
  2. waitAfter one hour
  3. customthe organic layer was separated
  4. washwashed with 5% aqueous sodium thiosulfate and brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d68b9eb14e884d96b66886df4ca5919f
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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