Lithium hydroxide, monohydrate → HCID 117771171, compound

HRID 2201531Notes

Reaction equation

HRID 2201531 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[N:32]=[C:31]([C:33]([O:35]C)=[O:34])[C:30]([O:37][CH3:38])=[CH:29][CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.O[Li].O>O1CCOCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH3:26])[S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([C:27]4[N:32]=[C:31]([C:33]([OH:35])=[O:34])[C:30]([O:37][CH3:38])=[CH:29][CH:28]=4)=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117771658HCID 117771658, compound

Product 1

HCID 117771171HCID 117771171, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of methyl 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-methoxypicolinate (400 mg, 0.74 mmol) in dioxane/H2O (10 mL/1 mL) was added LiOH.H2O (93 mg, 2.22 mmol) under N2 protection. The mixture was stirred at 70° C. for 3 h. The mixture was concentrated in vacuo and then extracted with EtOAc. After the organic layer was washed with HCl (a.q.), brine, dried over Na2SO4, filtered and evaporated, the crude product was purified by prep-TLC (PE:EtOAc=1:3) to give the product of 6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-3-methoxypicolinic acid (300 mg, yield: 77%). 1H-NMR (Methanol-d4, 400 MHz) δ 7.86˜7.90 (m, 2H), 7.80 (s, 1H), 7.69 (s, 1H), 7.65 (s, 1H), 7.55˜7.57 (m, 1H), 7.14 (t, J=8.8 Hz, 2H), 3.83 (s, 3H), 3.04 (s, 3H), 2.86 (s, 3H), 2.82 (s, 3H). MS (M+H)+: 528.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washAfter the organic layer was washed with HCl (a.q.), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude product was purified by prep-TLC (PE:EtOAc=1:3)

Sources & evidence

ORD record
ord-182bd171b94e4ed69777079bcec99a19
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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