3,5-Di-tert-butyl-4-hydroxybenzoic acid → HCID 23370131, compound

HRID 1901060Notes

Reaction equation

HRID 1901060 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([N:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:13])=[O:11].Cl.C(N=C=NCCCN(C)C)C.[C:33]([C:37]1[CH:38]=[C:39]([CH:43]=[C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:45]=1[OH:46])[C:40](O)=[O:41])([CH3:36])([CH3:35])[CH3:34]>ClCCl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([NH:9][C:10]([N:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:13])=[O:11])=[C:2]([NH:1][C:40](=[O:41])[C:39]2[CH:43]=[C:44]([C:47]([CH3:48])([CH3:49])[CH3:50])[C:45]([OH:46])=[C:37]([C:33]([CH3:36])([CH3:35])[CH3:34])[CH:38]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23370080HCID 23370080, compound

Product 1

HCID 23370131HCID 23370131, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(2-amino-4-fluorophenyl)-3-heptyl-3-methylurea (0.82 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride (0.67 g) and 3,5-di-t-butyl-4-hydroxybenzoic acid (0.88 g) dissolved in dichloromethane (10 ml) was stirred at room temperature overnight. The reaction solution was washed with water, saturated saline, dried over anhydrous MgSO4, and the solvent was distilled off. Purification of the residue by a silica gel column chromatography gave N-[5-fluoro-2-(3-heptyl-3-methylureido)phenyl]-3,5-di-t-butyl-4-hydroxybenzamide (0.84 g, 56%).

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. customPurification of the residue by a silica gel column chromatography

Sources & evidence

ORD record
ord-78d5073d88e244dfb6abc281e022bd2b
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

Loading…