Lithium Hydroxide → HCID 57441165, compound

HRID 1517111Notes

Reaction equation

HRID 1517111 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[CH:9][C:8]([CH3:21])=[C:7]([C:22]([N:24]2[CH2:29][CH2:28][CH:27]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:26][CH2:25]2)=[O:23])[N:6]=1)=[O:4].[OH-].[Li+]>C1COCC1.CO>[CH3:21][C:8]1[CH:9]=[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=1[C:22]([N:24]1[CH2:25][CH2:26][CH:27]([N:30]2[CH2:31][CH2:32][CH2:33][CH2:34]2)[CH2:28][CH2:29]1)=[O:23]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57441164HCID 57441164, compound

Product 1

HCID 57441165HCID 57441165, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 0.315 g (0.66 mmol) of 5-methyl-6-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-3-(3-trifluoromethyl-phenyl)-pyridine-2-carboxylic acid methyl ester (example 45) in 10 ml of THF/MeOH 1:1 were added 1.32 ml of lithium hydroxide (1 molar in H2O) and the reaction mixture was stirred at RT for 28 hours. Then, the solvents were evaporated and the residue was dissolved in H2O/CH2Cl2, neutralized with the help of hydrochloric acid and solid NaHCO3 and then extracted four times with CH2Cl2/2-propanol 3:1; the organic phases were dried over magnesium sulfate, filtered and evaporated, to give 0.188 g (62%) of the title compound as off-white solid. MS: 462.3 (MH+).

Workup

  1. customThen, the solvents were evaporated
  2. dissolutionthe residue was dissolved in H2O/CH2Cl2
  3. extractionextracted four times with CH2Cl2/2-propanol 3:1
  4. dry with materialthe organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-9f9d7faa745a42d4a87848288aa0dc8e
Source dataset
uspto-grants-2012_07
Patent number
US08227613B2

Reaction notes

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