Sodium Hydroxide → HCID 178425886, compound

HRID 1488133Notes

Reaction equation

HRID 1488133 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([O:12]C)=[O:11].[OH-].[Na+]>CO.O>[Cl:1][C:2]1[N:3]=[C:4]([CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178497715HCID 178497715, compound2×

Product 1

HCID 178425886HCID 178425886, compoundYield 107.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(4-chloro-2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)-4-methylbenzoate (compound 241.3, 290 mg, 0.87 mmol) in methanol (6 mL). Then a solution of sodium hydroxide (139 mg, 3.48 mmol) in water (3 mL) was added to the reaction. The reaction mixture was stirred for 1 h at 60° C., then concentrated under reduced pressure. The pH of the solution was adjusted to 1 with hydrogen chloride (2 M). The resulting mixture was concentrated under reduced pressure. Methanol (10 mL) was added to the residue. The salt was filtered off, and the filtrate was concentrated under reduced pressure to give 300 mg of the title compound as a brown solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. additionMethanol (10 mL) was added to the residue
  5. filtrationThe salt was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-298cc396d1794873be303c25a4f10925
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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