Sodium Hydroxide → HCID 57378659, compound

HRID 72553Notes

Reaction equation

HRID 72553 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[N:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:14]=3[C:15]([NH:17][C:18]3([C:21]4[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=4)[CH2:20][CH2:19]3)=[O:16])[CH2:10]2)=[N:6][CH:7]=1.[OH-].[Na+]>C1OCCOC1.O>[F:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[N:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][C:14]=3[C:15]([NH:17][C:18]3([C:21]4[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=4)[CH2:19][CH2:20]3)=[O:16])[CH2:10]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67958127Methyl 4-(1-(2-(3-((5-fluoropyrimidin-2-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoate

Product 1

HCID 57378659HCID 57378659, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of methyl 4-(1-(2-(3-((5-fluoropyrimidin-2-yl)oxy)azetidin-1-yl)-5-(trifluoromethyl)nicotinamido)cyclopropyl)benzoate (D182) (35 mg, 0.065 mmol) in a mixture 1-4 dioxane/water (3 ml/1 ml) 1M NaOH (0.098 ml, 0.098 mmol) was added. The mixture stirred 24 h at room temperature. After solvent evaporation, 1N HCl solution was added up to pH2. The solid precipitate was filtered off and washed with diethylether to afford the title compound (E48) (27 mg)

Workup

  1. customAfter solvent evaporation, 1N HCl solution
  2. additionwas added up to pH2
  3. filtrationThe solid precipitate was filtered off
  4. washwashed with diethylether

Sources & evidence

ORD record
ord-30983582d94644a68be5b423bb1e26b7
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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