Triethylamine → HCID 22132675, compound

HRID 1857282Notes

Reaction equation

HRID 1857282 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]3[C:35]4[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=4)[N:29]=[CH:28][CH:27]=3)=[CH:21][CH:20]=2)=[O:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][C:26]3[C:35]4[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=4)[N:29]=[CH:28][CH:27]=3)=[CH:23][CH:24]=2)=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22132762HCID 22132762, compound

Product 1

HCID 22132675HCID 22132675, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 22989253N,N-dimethylformamide ethyl acetateSolvent

Procedure

N-(4-Benzyloxyphenyl)-N'-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}urea (228 mg) was dissolved in N,N-dimethylformamide/ethyl acetate (15 ml/20 ml), after the addition of triethylamine (4 ml), 20% palladium hydroxide (1.18 g) was added, and the admixture was stirred at room temperature under hydrogen for 15 hours. The reaction mixture was filtered using Celite, after which the filtrate was concentrated, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 188 mg of the title compound (yield: 100%).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationafter which the filtrate was concentrated
  4. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-b4e2088e5c90426aa61810de5cc01e50
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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