3,5-Di-tert-butyl-4-hydroxybenzoic acid → HCID 23370097, compound

HRID 1901070Notes

Reaction equation

HRID 1901070 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:10].[C:19]([C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:31]=1[OH:32])[C:26](O)=[O:27])([CH3:22])([CH3:21])[CH3:20].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:12]([NH:11][C:9](=[O:10])[NH:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:1][C:26](=[O:27])[C:25]1[CH:29]=[C:30]([C:33]([CH3:34])([CH3:35])[CH3:36])[C:31]([OH:32])=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:24]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23370121HCID 23370121, compound

Product 1

HCID 23370097HCID 23370097, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-amino-3-pyridyl)-3-heptylurea (0.50 g), 3,5-di-t-butyl-4-hydroxybenzoic acid (0.60 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride (0.46 g) was stirred in dichloromethane (10 ml) at room temperature overnight. The reaction solution was washed with water, saturated saline and dried over anhydrous MgSO4. The solvent was distilled off and the residue was purified by a silica gel column chromatography (chloroform:methanol=20:1) to give N-[3-(3-heptylureido)-4-pyridyl]-3,5-di-t-butyl-4-hydroxybenzamide (0.15 g, 16%) as crystals.

Workup

  1. washThe reaction solution was washed with water, saturated saline
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by a silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-88670a67a7ba4e6499e9972505baa508
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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