2-Indancarboxylic Acid → 3-(2-Indanyl)carbonylamino-5-(4-methylphenyl)-pyrazole

HRID 1106615Notes

Reaction equation

HRID 1106615 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[NH:4][N:3]=1.[CH2:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH:15]1[C:23](O)=[O:24].Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][CH:15]1[C:23]([NH:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[NH:4][N:3]=1)=[O:24]

Participants

6

Reactant 3

HCID 5757772-Indancarboxylic AcidHCID 7367685-Amino-3-(4-methylphenyl)pyrazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 117589303-(2-Indanyl)carbonylamino-5-(4-methylphenyl)-pyrazoleYield 53%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-5-(4-methylphenyl)pyrazole (35 mg) and indan-2-carboxylic acid (33 mg) were dissolved in pyridine (2 ml) to which was subsequently added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (58 mg), and the mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate (30 ml), washed with water (30 ml), saturated aqueous sodium bicarbonate (30 ml) and saturated brine (30 ml) and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled away. The resulting crystalline residue was washed with ethyl ether to obtain the title compound (34 mg) as white crystals (melting point: 220-225° C.).

Workup

  1. washwashed with water (30 ml), saturated aqueous sodium bicarbonate (30 ml) and saturated brine (30 ml)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThen, the solvent was distilled away
  4. washThe resulting crystalline residue was washed with ethyl ether

Sources & evidence

ORD record
ord-4f58320b6f424e0a9326f68d5847da3e
Source dataset
uspto-grants-2000_05
Patent number
US06057335

Reaction notes

Loading…