Lithium Hydroxide → HCID 56960129, compound

HRID 539203Notes

Reaction equation

HRID 539203 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:20]=[C:21]([C:22]([O:24]C)=[O:23])[C:16]=2[N:15]=[C:14]1[C:32]([F:35])([F:34])[F:33].[OH-].[Li+]>C1COCC1>[CH3:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][N:13]1[C:17]2[CH:18]=[C:19]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:20]=[C:21]([C:22]([OH:24])=[O:23])[C:16]=2[N:15]=[C:14]1[C:32]([F:34])([F:33])[F:35]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 56960128methyl 1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-2-(trifluoromethyl)-1H-benzimidazole-4-carboxylate

Product 1

HCID 56960129HCID 56960129, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-2-(trifluoromethyl)-1H-benzimidazole-4-carboxylate, prepared as described in Example 46 (510 mg, 1.017 mmol) and 2 M lithium hydroxide (6 mL, 12.00 mmol) in THF (12 mL) was stirred at 50° C. for 2 h. The reaction was cooled to room temperature. The organic solvent was removed under reduced pressure and the aqueous was diluted with water and acidified by the addition of 1 N HCl. The precipitate formed was collected by filtration. The solid was washed with ether and turned into a gummy residue. The residue was washed with MeOH until all the material was transferred into the collection flask. The organics were evaporated and a white solid formed upon standing. The precipitate was collected by filtration, washed with water and dried to give the desired product (438 mg, 0.881 mmol, 87% yield) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.68 (d, J=2.02 Hz, 1H), 7.61 (d, J=8.08 Hz, 1H), 7.23 (t, J=7.83 Hz, 1H), 7.08 (d, J=2.02 Hz, 1H), 6.27 (d, J=7.58 Hz, 1H), 5.74 (s, 2H), 3.63-3.82 (m, 4H), 3.05-3.21 (m, 4H), 2.52 (br. s., 3H). MS (ES+) m/e 488 [M+H]+.

Workup

  1. customprepared
  2. temperatureThe reaction was cooled to room temperature
  3. customThe organic solvent was removed under reduced pressure
  4. additionthe aqueous was diluted with water
  5. additionacidified by the addition of 1 N HCl
  6. customThe precipitate formed
  7. filtrationwas collected by filtration
  8. washThe solid was washed with ether
  9. washThe residue was washed with MeOH until all the material
  10. customThe organics were evaporated
  11. customa white solid formed
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-cd93c615980846e5a9dfa57d1ef590a1
Source dataset
uspto-grants-2014_10
Patent number
US08865912B2

Reaction notes

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