Hydrochloric Acid → HCID 71263629, compound

HRID 1424864Notes

Reaction equation

HRID 1424864 reaction equation
I([O-])(=O)(=O)=O.[Na+].Cl.[Cl:8][C:9]1[CH:10]=[C:11]([N:26]([C:31]2[C:50]([CH:51]3[CH2:53][CH2:52]3)=[CH:49][C:34]3[C:35]([C:45]([NH:47][CH3:48])=[O:46])=[C:36]([C:38]4[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=4)[O:37][C:33]=3[CH:32]=2)[S:27]([CH3:30])(=[O:29])=[O:28])[CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][B:17]1[O:21]C(C)(C)C(C)(C)[O:18]1>C1COCC1.C(OCC)(=O)C>[Cl:8][C:9]1[CH:10]=[C:11]([N:26]([C:31]2[C:50]([CH:51]3[CH2:53][CH2:52]3)=[CH:49][C:34]3[C:35]([C:45](=[O:46])[NH:47][CH3:48])=[C:36]([C:38]4[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=4)[O:37][C:33]=3[CH:32]=2)[S:27]([CH3:30])(=[O:28])=[O:29])[CH:12]=[CH:13][C:14]=1[CH2:15][CH2:16][B:17]([OH:18])[OH:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 131732313HCID 131732313, compound

Product 1

HCID 71263629HCID 71263629, compoundYield 25.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium periodate (722 mg, 3.37 mmol) and 1N aqueous HCl (2.70 mL, 2.70 mmol) were added to a cold (0° C.) solution of 6-(N-(3-chloro-4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)phenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (150 mg, 0.225 mmol) in THF (3 mL). The mixture was stirred at 0° C. for 10 min and then warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with ethyl acetate. The organic layer was separated, 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 33 mg (25%) of the title compound as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.41-8.51 (m, 1H) 8.14 (s, 1H) 7.92-8.02 (m, 2H) 7.59 (s, 2H) 7.46-7.51 (m, 1H) 7.35-7.44 (m, 3H) 7.29-7.35 (m, 1H) 7.17 (s, 1H) 3.37 (s, 3H) 2.79-2.87 (m, 3H) 2.62-2.74 (m, 2H) 2.11-2.24 (m, 1H) 0.93-1.09 (m, 1H) 0.75-0.93 (m, 4H) 0.46 (m, 1H). LCMS (m/z, ES+)=585 (M+H+).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 1 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-9ceaacfedfac4c2e97cb7be259b64d9d
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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