Hydrochloric Acid → 3-Fluoro-4-(2-(5-(hydroxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinic acid

HRID 1685343Notes

Reaction equation

HRID 1685343 reaction equation
[F:1][C:2]1[C:3]([C:23]([O:25]C)=[O:24])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][N:16]=2)=[N:11][CH:10]=1.[OH-].[Na+].O.Cl>C1COCC1>[F:1][C:2]1[C:3]([C:23]([OH:25])=[O:24])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][N:16]=2)=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59200407Methyl 3-fluoro-4-(2-(5-(hydroxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate

Product 1

HCID 592004313-Fluoro-4-(2-(5-(hydroxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-fluoro-4-(2-(5-(hydroxymethyl)pyridin-2-ylamino)thiazol-5-ylthio)picolinate (0.750 g, 1.91 mmol) was dissolved in THF (20 mL) and treated with NaOH (5N, 2.5 mL, 12.5 mmol) at 23° C. The reaction was stirred for 2 hours, then water was added. The reaction was acidified with conc. HCl to pH ˜2. The solvent was evaporated and the residue was diluted with water. This was extracted with ethyl acetate/THF (3×) and the combined organic layers were then dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (0.630 g, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 4.46 (2H, s), 5.22 (1H, s), 7.04-7.12 (2H, m), 7.74 (1H, dd, J=8.34, 2.27 Hz), 7.84 (1H, br s) 8.24 (1H, d, J=1.52 Hz), 8.31 (1H, d, J=5.05 Hz), 11.89 (1H, s), 13.75 (1H, s). LC/MS (M+H)+: 379. HPLC ret. time (Condition N): 2.463 min.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water
  3. extractionThis was extracted with ethyl acetate/THF (3×)
  4. dry with materialthe combined organic layers were then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9425acc47a2a4ec68595038ea3cc7f62
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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