4-Cyclohexylbenzenamine → 1-[3-(4-Cyclohexylphenylamino)pyrido[2,3-b]pyrazin-6-yl]-3-ethylurea

HRID 1511828Notes

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.[CH:18]1([C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:18]1([C:24]2[CH:25]=[CH:26][C:27]([NH:28][C:2]3[N:7]=[C:6]4[N:8]=[C:9]([NH:12][C:13]([NH:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:5]4=[N:4][CH:3]=3)=[CH:29][CH:30]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

83 mg of 1-(3-chloropyrido[2,3-b]pyrazin-6-yl)-3-ethylurea (0.33 mmol), 99 mg of 4-cyclohexylaniline (0.55 mmol), 30 mg of sodium tert-butoxide (0.30 mmol), 29 mg of tris(dibenzylideneacetone)dipalladium(0) (0.03 mmol) and 68 mg of 2-(dicyclohexylphosphanyl)biphenyl (0.19 mmol) were initially charged in 1.5 ml of dried toluene. The reaction mixture was heated to 100° C. under nitrogen in a microwave (100 watt) for 30 minutes. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (dichloromethane/methanol eluent). This gave a yellow solid.

Workup

customThe solvent was removed under reduced pressure
customthe crude product was purified by column chromatography on silica gel (dichloromethane/methanol eluent)
customThis gave a yellow solid

Sources & evidence

ORD record: ord-1cbedc6fa9bb49058ff175d127bc62ad
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217042B2

Reaction notes

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