Hydrochloric Acid → HCID 59411416, compound

HRID 2068426Notes

Reaction equation

HRID 2068426 reaction equation
[F:1][C:2]1[C:3]2[N:4]([N:21]=[C:22]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:23]=2[C:24](=[O:27])[NH:25][CH3:26])[CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([CH3:20])=[N:10][C:11]([O:18][CH3:19])=[C:12]([CH:17]=1)[C:13]([O:15]C)=[O:14].[OH-].[Na+].Cl>O1CCOCC1>[F:1][C:2]1[C:3]2[N:4]([N:21]=[C:22]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[C:23]=2[C:24](=[O:27])[NH:25][CH3:26])[CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([CH3:20])=[N:10][C:11]([O:18][CH3:19])=[C:12]([CH:17]=1)[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59411422Methyl 5-[4-fluoro-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]pyrazolo[1,5-a]pyridin-5-yl]-2-methoxy-6-methyl-3-pyridinecarboxylate

Product 1

HCID 59411416HCID 59411416, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution containing Methyl 5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxy-6-methylnicotinate (0.041 g, 0.088 mmol) and dioxane (0.44 mL) was added aqueous sodium hydroxide (0.44 mL, 2.0 M). The solution was maintained at room temperature for 18 h. The solution was adjusted to below pH 4 with aqueous HCl (1.0 mL, 1.0 N). 5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxy-6-methylnicotinic acid precipitated as a white solid and was filtered off, washed with water (3×2 mL) and air dried. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.98 (1H, br. s.), 8.73 (1H, d, J=7.03 Hz), 8.44 (1H, q, J=4.52 Hz), 8.06 (1H, s), 7.87-7.98 (2H, m), 7.29-7.39 (2H, m), 7.04 (1H, t, J=7.03 Hz), 3.98 (3H, s), 2.76 (3H, d, J=4.52 Hz), 2.42 (3H, s). LCMS retention time: 1.798 min. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna, 3 micron, C18, 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 5% CH3CN/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% CH3CN/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. m/z 453 (MH+).

Workup

  1. custom5-(4-fluoro-2-(4-fluorophenyl)-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxy-6-methylnicotinic acid precipitated as a white solid
  2. filtrationwas filtered off
  3. washwashed with water (3×2 mL) and air
  4. customdried
  5. customequipped with a Phenomenex-Luna, 3 micron, C18, 2.0×50 mm column
  6. washThe elution conditions
  7. customa gradient time of 4 min
  8. customa hold time of 1 min
  9. customan analysis time of 5 min where solvent A was 5% CH3CN/95% H2O/10 mM ammonium acetate and solvent B

Sources & evidence

ORD record
ord-e5a92a4182ab47fc854466e1e8115c4b
Source dataset
uspto-grants-2012_10
Patent number
US08293909B2

Reaction notes

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