Hydrochloric Acid → HCID 117771339, compound

HRID 2201582Notes

Reaction equation

HRID 2201582 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:41]([O:43]C)=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:38])=[O:37])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]1[C:10]([C:41]([OH:43])=[O:42])=[N:11][C:12]([C:15]2[C:16]([N:35]([CH3:40])[S:36]([CH3:39])(=[O:37])=[O:38])=[CH:17][C:18]3[O:22][C:21]([C:23]4[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=4)=[C:20]([C:30](=[O:33])[NH:31][CH3:32])[C:19]=3[CH:34]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117771053HCID 117771053, compound

Product 1

HCID 117771339HCID 117771339, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinate (430 mg, 0.70 mmol) in MeOH (4 mL) was added 1N NaOH (2.10 ml, 2.09 mmol). The resulting mixture was stirred at RT overnight, then added 1N HCl (2.10 ml, 2.09 mmol) was added. The reaction was concentrated in vacuo. The resulting residue was treated with EtOH/DCM (1:1) and filtered to remove the solid. The filtrate was concentrated in vacuo to provide 3-(benzyloxy)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)picolinic acid (430 mg, yield: 102%). MS (M+H)+: 604.

Workup

  1. additionwas added
  2. concentrationThe reaction was concentrated in vacuo
  3. additionThe resulting residue was treated with EtOH/DCM (1:1)
  4. filtrationfiltered
  5. customto remove the solid
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5cefb7a2eff24a9985f27d09d8f978bf
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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