Sodium Hydroxide → HCID 90028965, compound

HRID 1488096Notes

Reaction equation

HRID 1488096 reaction equation
[C:1]([C:3]1[N:4]=[C:5]([CH2:20][OH:21])[NH:6][C:7]=1[C:8]1[C:9]([CH3:19])=[CH:10][C:11]([CH3:18])=[C:12]([CH:17]=1)[C:13]([O:15]C)=[O:14])#[N:2].[OH-].[Na+]>CO.O>[C:1]([C:3]1[N:4]=[C:5]([CH2:20][OH:21])[NH:6][C:7]=1[C:8]1[C:9]([CH3:19])=[CH:10][C:11]([CH3:18])=[C:12]([CH:17]=1)[C:13]([OH:15])=[O:14])#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 90029673HCID 90029673, compound2×

Product 1

HCID 90028965HCID 90028965, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Into a 25-mL round-bottom flask, was placed a solution of methyl 5-(4-cyano-2-(hydroxymethyl)-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 219.6, 100 mg, 0.35 mmol) in methanol (10 mL) and a solution of NaOH (0.14 g, 3.5 mmol) in water (5 mL). The reaction mixture was stirred for 15 h at room temperature, then concentrated under reduced pressure. The pH of the solution was adjusted to 1-2 with hydrogen chloride (4 M). The resulting mixture was concentrated under reduced pressure. Methanol (5 mL) was added to the residue. The salt was filtered off, and the filtrate was concentrated under reduced pressure to give 200 mg (crude) of the title compound as a light yellow solid.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. additionMethanol (5 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-79966485d61a46349779a21226cbf4a1
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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