Hydrochloric Acid → 4-(2-(6-Chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinic acid

HRID 1685359Notes

Reaction equation

HRID 1685359 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[S:11][C:12]([S:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24]C)=[O:23])[CH:17]=3)=[CH:13][N:14]=2)[CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[S:11][C:12]([S:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([C:22]([OH:24])=[O:23])[CH:17]=3)=[CH:13][N:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59200387Methyl 4-(2-(6-chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinate

Product 1

HCID 592003834-(2-(6-Chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinic acidYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of methyl 4-(2-(6-chloro-2-methylpyrimidin-4-ylamino)thiazol-5-ylthio)picolinate (292 mg, 0.741 mmol) in THF (8 mL) was added NaOH (8 mL, 1M in water). After 6 h, the reaction was acidified with 10% HCl to pH ˜6 at which time a solid precipitated. The solid was collected by filtration, washed with water and allowed to dry overnight to give the title material (239 mg, 85%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm: 12.55 (1H, s), 8.33 (1H, d, J=5.31 Hz), 7.84 (1H, s), 7.57 (1H, d, J=1.77 Hz), 7.16 (1H, dd, J=5.31, 2.02 Hz), 6.90 (1H, s), 2.51 (3H, s). LC/MS (M+H)+: 380, 382. HPLC ret. time (Condition I): 1.175 min.

Workup

  1. customprecipitated
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customto dry overnight

Sources & evidence

ORD record
ord-82971a67c1ff459c816f56e3bccb6e68
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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