Methanol → HCID 178428092, compound

HRID 526442Notes

Reaction equation

HRID 526442 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:23]3[CH:32]=[C:31]([CH3:33])[C:26]([C:27]([O:29]C)=[O:28])=[CH:25][N:24]=3)[C:13]=2[O:14]COCC[Si](C)(C)C)=[CH:5][CH:4]=1)#[N:2].CO.[Li+].[OH-]>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:23]3[CH:32]=[C:31]([CH3:33])[C:26]([C:27]([OH:29])=[O:28])=[CH:25][N:24]=3)[C:13]=2[OH:14])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 131732879HCID 131732879, compound

Product 1

HCID 178428092HCID 178428092, compoundYield 51.76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Combined methyl 6-(4-(4-cyanophenyl)-5-((2-(trimethylsilyl)ethoxy)methoxy)-1H-pyrazol-1-yl)-4-methylnicotinate (8.67 g, 25.96 mmol), methanol (50 mL), water (50 mL) and LiOH (3.27 g, 77.87 mmol). The reaction mixture was stirred at room temperature for 6 h and at 50° C. overnight. The reaction mixture was concentrated to remove most of the methanol and then the pH was adjusted to 3 by addition of 3N HCl to give a solid. The solid was collected by filtration and dried in vacuum to give the title compound (4.3 g, 51.76%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove most of the methanol
  3. additionthe pH was adjusted to 3 by addition of 3N HCl
  4. customto give a solid
  5. filtrationThe solid was collected by filtration
  6. customdried in vacuum

Sources & evidence

ORD record
ord-85f4de8fe2af426e9d5430ded509347b
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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