Sodium Hydroxide → HCID 178494614, compound

HRID 1871537Notes

Reaction equation

HRID 1871537 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH2:10][NH:11][C:12]2[C:16]([CH2:17][OH:18])=[CH:15][NH:14][N:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:19]=[CH:20][C:21]=2[O:22][CH3:23])[CH2:10][NH:11][C:12]2[C:16]([CH2:17][O:18][CH3:25])=[CH:15][NH:14][N:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 1784910433-(3-Cyclopentyloxy-4-methoxybenzylamino)-4-hydroxymethylpyrazole

Product 1

HCID 178494614HCID 178494614, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3-cyclopentyloxy-4-methoxybenzylamino)-4-hydroxymethylpyrazole (1.0 g, 3.15 mmol) and p-toluenesulfonic acid monohydrate (0.2 g, 1.0 mmol) in methanol (100 mL) was kept at room temperature for 10 min. The reaction mixture was neutralized with 1 N aqueous sodium hydroxide and evaporated under reduced pressure at room temperature. The residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (10 mL). The combined ethyl acetate layers were washed with water and evaporated under reduced pressure. The residue was taken up in a small volume of methylene chloride and applied to a 4 mm silica gel disk on a Chromatotron. Elution with 525 mL of methylene chloride and 275 mL of 1% methanol/methylene chloride removed some impure material. Continued elution with 75 mL of 1% methanol/methylene chloride afforded 380 mg (36%) of pure 3-(3-cyclopentyloxy-4-methoxybenzylamino)-4-methyoxymethylpurazole, mp. 112-115°.

Workup

  1. customevaporated under reduced pressure at room temperature
  2. customThe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (10 mL)
  5. washThe combined ethyl acetate layers were washed with water
  6. customevaporated under reduced pressure
  7. washElution with 525 mL of methylene chloride and 275 mL of 1% methanol/methylene chloride
  8. customremoved some impure material
  9. washelution with 75 mL of 1% methanol/methylene chloride
  10. customafforded 380 mg (36%) of pure 3-(3-cyclopentyloxy-4-methoxybenzylamino)-4-methyoxymethylpurazole, mp. 112-115°

Sources & evidence

ORD record
ord-08b0017829594762a81f73aa601ebb61
Source dataset
uspto-grants-2000_08
Patent number
US06103749

Reaction notes

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