Hydrochloric Acid → HCID 90333589, compound

HRID 595693Notes

Reaction equation

HRID 595693 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:21]=[C:22]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:23]([C:24]([O:26]C)=[O:25])=[C:11]2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O.Cl>O1CCOCC1.O.O>[CH2:1]([O:8][C:9]1[C:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:21]=[C:22]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:23]([C:24]([OH:26])=[O:25])=[C:11]2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 90333634HCID 90333634, compound

Product 1

HCID 90333589HCID 90333589, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of methyl 5-(benzyloxy)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylate (3 g, 6.2 mmol) in dioxane/H2O (1/1, 60 mL) was added LiOH.H2O (781 mg, 19 mmol), and the mixture was heated to reflux for 3 hours, and concentrated in vacuo. The residue obtained was dissolved in H2O, 1 N HCl was added until pH reached 3, and the resulting precipitate was collected by filtration, washed with water, dried to afford 5-(benzyloxy)-2-(4-fluorophenyl)-6-(N-methylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxylic acid (2.8 g, yield: 96%). 1H-NMR (DMSO-d6, 400 MHz) δ 12.4 (s, 1H), 8.97 (s, 1H), 7.74˜7.77 (m, 2H), 7.59 (s, 1H), 7.54 (d, J=7.2 Hz, 2H), 7.29˜7.43 (m, 3H), 7.26 (t, J=8.8 Hz, 2H), 5.32 (s, 2H), 3.54 (s, 3H), 3.20 (s, 3H), 3.00 (s, 3H). MS (M+H)+: 470.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue obtained
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-9604a91bb24f4afcbe3cc60c620efc2e
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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