Hydrochloric Acid → HCID 66803490, compound

HRID 341559Notes

Reaction equation

HRID 341559 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O>[F:16][C:13]([F:14])([F:15])[CH2:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66802732HCID 66802732, compound2×

Product 1

HCID 66803490HCID 66803490, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5-(2,2,2-Trifluoroethylamino)-pyridine-2-carboxylic acid methyl ester (Intermediate 280, 75 mg, 0.320 mmol) was dissolved in a mixture of THF (0.75 mL) and water (0.25 mL) and lithium hydroxide monohydrate (27 mg, 0.640 mmol) was added. The mixture was stirred at room temperature for 18 h. The mixture was diluted with water (5 mL), brought to approximately pH 4 by the addition of 1M HCl, then extracted with DCM (4×9 mL). The combined organic extracts were washed with brine (5 mL), dried over sodium sulfate and evaporated under vacuum to afford the title compound as a white solid (51 mg, 72%). Method B HPLC-MS: MH+ requires m/z=221. Found: m/z=221, Rt=1.30 min (100%).

Workup

  1. additionwas added
  2. extractionextracted with DCM (4×9 mL)
  3. washThe combined organic extracts were washed with brine (5 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-4e1b442caee242688910d21ca7d2e66b
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

Loading…