Lithium hydroxide, monohydrate → 6-(Trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylic acid

HRID 570179Notes

Reaction equation

HRID 570179 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:13]=[N:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]2[CH:18]=1)=[O:5])C.O.[OH-].[Li+]>O1CCCC1.O>[F:17][C:14]([F:15])([F:16])[C:11]1[N:12]=[CH:13][C:8]2[N:9]([CH:18]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67516905Ethyl 6-(trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylate

Product 1

HCID 675171956-(Trifluoromethyl)imidazo[1,2-a]pyrazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step A was dissolved in tetrahydrofuran (10 mL) and a solution of lithium hydroxide monohydrate (97 mg, 8.3 mmol) in water (5 mL) was added. The reaction mixture was stirred at room temperature for one hour, after which time the tetrahydrofuran was removed on a rotary evaporator under reduced pressure, and water was added (5 mL), followed by the addition of 1 N HCl (5 mL). The resulting suspension was filtered through a glass-fritted filter funnel, and the isolated solid was washed with water and dried over nitrogen to afford 451 mg of the title compound as a solid. 1H NMR ((CD3)2SO) δ 9.33 (s, 1H), 9.30 (s, 1H), 8.69 (s, 1H).

Workup

  1. customafter which time the tetrahydrofuran was removed on a rotary evaporator under reduced pressure, and water
  2. additionwas added (5 mL)
  3. additionfollowed by the addition of 1 N HCl (5 mL)
  4. filtrationThe resulting suspension was filtered through a glass-fritted filter funnel
  5. washthe isolated solid was washed with water
  6. customdried over nitrogen

Sources & evidence

ORD record
ord-eceb0fc2d420412e8c47a5e898a646ba
Source dataset
uspto-grants-2015_05
Patent number
US09023850B2

Reaction notes

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