O-Toluidine → HCID 58881852, compound

HRID 1428200Notes

Reaction equation

HRID 1428200 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:5]2=[N:4][CH:3]=1.[NH2:18][C:19]1[C:20]([CH3:25])=[CH:21][CH:22]=[CH:23][CH:24]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>C1(C)C=CC=CC=1>[CH2:16]([NH:15][C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:5]2[C:6]([N:8]=1)=[N:7][C:2]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])=[CH:3][N:4]=2)=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 588817911-(3-Chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea

Product 1

HCID 58881852HCID 58881852, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

55 mg 1-(3-chlor-pyrido[2,3-b]pyrazine-6-yl)-3-ethyl-urea (0.22 mmol), 60 mg o-toluidine (0.56 mmol), 33 mg sodium-tert.-butylate(0.33 mmol), 29 mg tris(dibenzalacetone)palladium(0) (0.03 mmol) and 78 mg 2-(dicyclohexylphosphanyl)biphenyl (0.22 mmol) were presented in 1.5 ml predried toluene in a microwave reaction vessel under nitrogen as protective gas. The reaction mass was heated in the microwave at 100° C. (100 watt) for 30 minutes. Then the volatile components were removed in vacuum and the raw product was cleaned using column chromatography on silica gel (solvent dichloromethane/methanol). A yellow solid was obtained.

Workup

  1. customThen the volatile components were removed in vacuum
  2. customA yellow solid was obtained

Sources & evidence

ORD record
ord-f0ed41ad86cc4cd7b295524b91a424ba
Source dataset
uspto-grants-2015_01
Patent number
US08937068B2

Reaction notes

Loading…