Lithium Hydroxide → HCID 118590619, compound

HRID 1054471Notes

Reaction equation

HRID 1054471 reaction equation
C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([N:15]3[CH2:19][CH2:18][CH2:17][CH:16]3[C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[O:27][C@@H:28]3[CH2:32][CH2:31][O:30][CH2:29]3)[CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)=[O:5])C.[Li+].[OH-]>C(O)C>[F:26][C:24]1[CH:23]=[CH:22][C:21]([O:27][C@@H:28]2[CH2:32][CH2:31][O:30][CH2:29]2)=[C:20]([CH:16]2[CH2:17][CH2:18][CH2:19][N:15]2[C:12]2[CH:13]=[CH:14][C:9]3[N:10]([C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=3)[CH:11]=2)[CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 118590427HCID 118590427, compound

Product 1

HCID 118590619HCID 118590619, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To stirred solution of Ethyl-6-(2-(5-fluoro-2-(((R)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylate (1.15 g, 26.18 mmol) in ethanol was added 1M LiOH (2.3 ml) solution and stirred for 5 h at 85° C. Solvent was removed under reduced pressure and residue was dissolved in water, extracted unwanted impurities with diethyl ether and water was acidified with 2N HCl and solid was collected by filtration. Solid was dried under high vacuum to afford 6-(2-(5-fluoro-2-(((R)-tetrahydrofuran-3-yl)oxy)phenyl)pyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxylic acid as pale yellow solid (400 mg, yield: 37.7%), MS (ESI): 412.1 (M+H).

Workup

  1. customSolvent was removed under reduced pressure and residue
  2. dissolutionwas dissolved in water
  3. extractionextracted unwanted impurities with diethyl ether and water
  4. filtrationwas collected by filtration
  5. customSolid was dried under high vacuum

Sources & evidence

ORD record
ord-dae85431347e4d40b8992d32c591ec1a
Source dataset
uspto-grants-2016_07
Patent number
US09394305B2

Reaction notes

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