Water → HCID 70941574, compound

HRID 2402342Notes

Reaction equation

HRID 2402342 reaction equation
[OH-].[Na+].O.C([O:6][C:7]([C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[C:11]2[N:21]=[C:22]([N:24]3[CH2:29][CH2:28][C:27]([F:31])([F:30])[CH2:26][CH2:25]3)[S:23][C:10]=12)=[O:8])C>O1CCOCC1>[F:31][C:27]1([F:30])[CH2:28][CH2:29][N:24]([C:22]2[S:23][C:10]3[C:11]([N:21]=2)=[N:12][C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:14][C:9]=3[C:7]([OH:8])=[O:6])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 71059752HCID 71059752, compound

Product 1

HCID 70941574HCID 70941574, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

An aqueous solution of 4 mol/L sodium hydroxide (1.55 mL, 6.20 mmol) and water (1 mL) were added to a solution of 2-(4,4-difluoropiperidino)-5-phenyl-7-thiazolo[4,5-b]pyridinecarboxylic acid ethyl ester (500 mg, 1.24 mmol) prepared above in 1,4-dioxane (5 mL), followed by stirring at room temperature for 3 hr. The reaction solution was concentrated, and a saturated aqueous solution of ammonium chloride was added to the residue. The precipitated crystals were collected by filtration, washed with water, and dried. The resulting crude crystals were subjected to recrystallization from acetic acid-water to obtain the title compound (442 mg, 1.18 mmol) as a yellow powder.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiona saturated aqueous solution of ammonium chloride was added to the residue
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe resulting crude crystals were subjected to recrystallization from acetic acid-water

Sources & evidence

ORD record
ord-677822ca17d640b98fd93c678ffc00cc
Source dataset
uspto-grants-2014_08
Patent number
US08796320B2

Reaction notes

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