Triethylamine → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(1H-2-imidazolyl)urea

HRID 387704Notes

Reaction equation

HRID 387704 reaction equation
[NH2:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.[C:14]1([O:20]C(Cl)=O)C=CC=CC=1.[NH2:24][C:25]1[CH:48]=[CH:47][C:28]([O:29][C:30]2[C:39]3[C:34](=[CH:35][C:36]([O:42][CH2:43][CH2:44][O:45][CH3:46])=[C:37]([C:40]#[N:41])[CH:38]=3)[N:33]=[CH:32][CH:31]=2)=[CH:27][CH:26]=1>CN(C)C=O.O.C(OCC)(=O)C>[C:40]([C:37]1[CH:38]=[C:39]2[C:34](=[CH:35][C:36]=1[O:42][CH2:43][CH2:44][O:45][CH3:46])[N:33]=[CH:32][CH:31]=[C:30]2[O:29][C:28]1[CH:27]=[CH:26][C:25]([NH:24][C:14]([NH:1][C:2]2[NH:3][CH:4]=[CH:5][N:6]=2)=[O:20])=[CH:48][CH:47]=1)#[N:41]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 821402-AminoimidazoleHCID 229365064-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 22936541N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-(1H-2-imidazolyl)ureaYield 9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 2-aminoimidazole (132 mg, 1.0 mmol) in a dimethylformamide (2 ml) and water (1 ml) mixed solvent, triethylamine (0.42 ml, 3.0 mmol) and phenylchloroformate (0.14 ml, 1.1 mmol) were added at room temperature, and the mixture was stirred for 10 minutes. After further adding 4-(4-aminophenoxy)-7-(2-methoxyethoxy)-6-cyanoquinoline (168 mg, 0.5 mmol), the mixture was stirred overnight. The reaction solution was diluted with ethyl acetate (30 ml) and then washed with water (10 ml×2) and saturated saline (10 ml), and the organic layer was dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent-ethyl acetate:ethanol=95:5) to obtain the title compound (20 mg, 0.045 mmol, 8.98%) as white crystals.

Workup

  1. additionwere added at room temperature
  2. stirringthe mixture was stirred overnight
  3. washwashed with water (10 ml×2) and saturated saline (10 ml)
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent-ethyl acetate:ethanol=95:5)

Sources & evidence

ORD record
ord-abc20db744914668a404cb2526b06df9
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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