Sodium Hydroxide → HCID 66725242, compound

HRID 1888793Notes

Reaction equation

HRID 1888793 reaction equation
[CH3:1][C:2]1[N:3]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:4](=[O:27])[C:5]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[O:14])=[CH:6][C:7]=1[C:8]([O:10]CC)=[O:9].[OH-].[Na+]>C1COCC1.O>[CH3:26][S:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][NH:15][C:13]([C:5]2[C:4](=[O:27])[N:3]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:36])([F:35])[F:37])[CH:29]=3)[C:2]([CH3:1])=[C:7]([C:8]([OH:10])=[O:9])[CH:6]=2)=[O:14])=[CH:22][CH:21]=1)(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 66725440HCID 66725440, compound

Product 1

HCID 66725242HCID 66725242, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-5-({[4-(methylsulfonyl)benzyl]amino}carbonyl)-6-oxo-1-[3-(trifluoromethyl)phenyl]-1,6-dihydropyridine-3-carboxylate (0.70 g, 1.30 mmol) in THF (10 ml) and water (10 ml) was added NaOH (1M, 2 ml, 2 mmol), and the mixture was stirred for 1 h at room temperature, monitoring the progress of the reaction by LC-MS. 20% conversion was observed and another portion of NaOH (1M, 1 ml, 1 mmol) was added, and the reaction was allowed to run for another hour. This process was repeated until complete conversion of the ester was observed (normally 3-4 hours). The outcome of the reaction is two compounds with the same mass, in a 95:5 proportion. The main product is the subtitle compound, and the other is a regioisomer. The reaction mixture was evaporated in order to remove TIM, and the residual water solution was acidified and then extracted into EtOAc. The organic phase was collected and dried over Na2SO4. Filtration and evaporation gave a crude product 0.60 g (90%) of a yellowish solid, which was used further without purification. A portion of the product was purified using preparative HPLC.

Workup

  1. customthe progress of the reaction by LC-MS
  2. waitto run for another hour
  3. customnormally 3-4 hours

Sources & evidence

ORD record
ord-e5dcf4fb7d9f4c389d891bb295d46633
Source dataset
uspto-grants-2013_08
Patent number
US08501784B2

Reaction notes

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