Sodium Hydroxide → N-{4-[2-(1-Hydroxyethyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl}propanamide

HRID 1727377Notes

Reaction equation

HRID 1727377 reaction equation
[OH-].[Na+].C([O:11][CH:12]([C:14]1[S:15][C:16]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:36])[CH2:34][CH3:35])[CH:27]=2)=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)[N:18]=1)[CH3:13])(=O)C1C=CC=CC=1>CO.O1CCCC1>[OH:11][CH:12]([C:14]1[S:15][C:16]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:36])[CH2:34][CH3:35])[CH:27]=2)=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=2)[N:18]=1)[CH3:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 534280501-[4-(3-Methylphenyl)-5-(2-propanamidopyridin-4-yl)-1,3-thiazol-2-yl]ethyl benzoate

Product 1

HCID 53432117N-{4-[2-(1-Hydroxyethyl)-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl}propanamideYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

An 1N aqueous sodium hydroxide solution was added dropwise to a solution of 1-[4-(3-methylphenyl)-5-(2-propionylamino-4-pyridyl)-1,3-thiazol-2-yl]ethyl benzoate (1.63 g, 3.46 mmol) in methanol (5 mL) and tetrahydrofuran (20 mL) at 0° C. and the reaction mixture was allowed to warm up to room temperature. The resulting mixture was stirred at room temperature for 30 minutes and the solvent was removed under reduced pressure. The residue was treated with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extracts were washed with aqueous sodium hydrogen carbonate solution and brine. The resulting solution was dried, and concentrated under reduced pressure. The obtained crude crystal was recrystallized from ethyl acetate-hexane to give a title compound (1.12 g, yield 89%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionThe residue was treated with aqueous sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with aqueous sodium hydrogen carbonate solution and brine
  5. customThe resulting solution was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crude crystal
  8. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a726da6ed23f431289c1133c010c2371
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

Loading…