Sodium Hydroxide → 5-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid

HRID 1643629Notes

Reaction equation

HRID 1643629 reaction equation
C[O:2][C:3]([C:5]1[C:10]([F:11])=[CH:9][C:8]([O:12][C:13]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[CH:16]=[C:15]([C:24](=[O:32])[NH:25][C:26]3[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=3)[CH:14]=2)=[CH:7][N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1>[CH3:22][C:20]1([CH3:23])[CH2:19][C:18]2[C:13]([O:12][C:8]3[CH:9]=[C:10]([F:11])[C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)=[CH:14][C:15]([C:24](=[O:32])[NH:25][C:26]3[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=3)=[CH:16][C:17]=2[O:21]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59559964Methyl 5-[[2,3-dihydro-2,2-dimethyl-6-[[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl]-4-benzofuranyl]oxy]-3-fluoro-2-pyridinecarboxylate

Product 1

HCID 595600475-[2,2-Dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-[2,2-dimethyl-6-(1-methyl-1H-pyrazol-3-ylcarbamoyl)-2,3-dihydro-benzofuran-4-yloxy]-3-fluoro-pyridine-2-carboxylic acid methyl ester (175b) (949 mg, 2.15 mmol) in 12 mL THF was added 4 mL of 1.0 N aqueous NaOH. The mixture was heated at 60° C. for 1 hr, and concentrated in vacuo. The residue was acidified to pH ˜1 with 1N aqueous HCl, filtered, washed with water, and dried under vacuum at 60° C. overnight to give an off-white solid (800 mg, 87% yield). LCMS for C21H19FN4O5 m/z 427.20 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. washwashed with water
  4. customdried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-8c7dad9eb73a430c886eb31e46e6cc44
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…