Dimethyl Sulfoxide → 4-chloro-3-((trifluoromethyl)phenyl)-N'-(4-(N-(3-(N-(3-pyridyl)carbamoyl)phenyl)carbamoyl)phenyl)urea

HRID 491097Notes

Reaction equation

HRID 491097 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:9](=[O:11])[NH2:10])=[CH:4][C:3]=1C(O)=O.[NH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1.C(Cl)Cl.CS(C)=O.[CH2:39]1[CH2:43][O:42][CH2:41][CH2:40]1>ClCCCl>[Cl:1][C:2]1([C:9](=[O:11])[NH:8][C:5]2[CH:6]=[CH:41][CH:40]=[C:39]([C:43](=[O:42])[NH:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH:4]=2)[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:20])([F:21])[F:19])[C:9](=[O:11])[NH2:10])=[CH:4][CH2:3]1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 100093-AminopyridineHCID 865836134-chloro-3-((trifluoromethyl)phenyl)-N'-(3-carboxyphenyl)urea

Product 1

HCID 865836124-chloro-3-((trifluoromethyl)phenyl)-N'-(4-(N-(3-(N-(3-pyridyl)carbamoyl)phenyl)carbamoyl)phenyl)ureaYield 59%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
36 °C

Procedure

A mixture of N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(3-carboxyphenyl) urea (Method C1f; 0.030 g, 0.067 mmol) and N-cyclohexyl-N′-(methylpolystyrene)carbodiimide (55 mg) in 1,2-dichloroethane (1 mL) was treated with a solution of 3-aminopyridine in CH2Cl2 (1 M; 0.074 mL, 0.074 mmol). (In cases of insolubility or turbidity, a small amount of DMSO was also added.) The resulting mixture was heated at 36° C. overnight. Turbid reactions were then treated with THF (1 mL) and heating was continued for 18 h. The resulting mixtures were treated with poly(4-(isocyanatomethyl)styrene) (0.040 g) and the resulting mixture was stirred at 36° C. for 72 h, then cooled to room temp. and filtered. The resulting solution was filtered through a plug of silica gel (1 g). Concentration under reduced pressure afforded N-(4-chloro-3-((trifluoromethyl)phenyl)-N′-(4-(N-(3-(N-(3-pyridyl)carbamoyl)phenyl)carbamoyl)phenyl) urea (0.024 g, 59%): TLC (70% EtOAc/30% hexane) Rf0.12.

Workup

  1. temperatureheating
  2. temperaturecooled to room temp.
  3. filtrationfiltered
  4. filtrationThe resulting solution was filtered through a plug of silica gel (1 g)
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-18d0bd2f95d248ca9b331a72d4da600b
Source dataset
uspto-grants-2009_05
Patent number
US07528255B2

Reaction notes

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