Triethylamine → 3-[1-(4-Methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-propionic acid hydrochloride

HRID 5015

Reaction equation

HRID 5015 reaction equation
O=[C:2]([CH2:8][C:9](=O)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].CCN(CC)CC.[ClH:24].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=1>CO>[ClH:24].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:9]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][C:2]([CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[N:34]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 151691084,6-Dioxo-6-(3-pyridyl)hexanoic acid

Product 1

HCID 678573363-[1-(4-Methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-propionic acid hydrochlorideYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 29 (2.21 g, 10 mM) in methanol (150 ml) containing Et3N (2 ml) was treated with 4-methoxyphenylhydrazine hydrochloride (1.85 g, 10.6 mM) at RT for 4 hr. The solvent was removed in vacuo and the residue was partitioned between 5% NaOH and Et2O. The basic aqueous layer was separated and acidified with 10% HCl to pH 2. Saturated brine was added and the aqueous layer was exhaustively extracted with CH2Cl2. The combined CH2Cl2 layers were concentrated to give the title compound 31 as a tan crystalline solid (Recry. Acetone, 1.87 g, 52%) mp=226°-228° C., MS, m/e 323 (M+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between 5% NaOH and Et2O
  3. customThe basic aqueous layer was separated
  4. additionSaturated brine was added
  5. extractionthe aqueous layer was exhaustively extracted with CH2Cl2
  6. concentrationThe combined CH2Cl2 layers were concentrated

Sources & evidence

ORD record
ord-cbbe96bf61684243a07da170a8302318
Source dataset
uspto-grants-1993_09
Patent number
US05242940

Linked notes

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