Benzenamine, 4-(4-morpholinyl)- → HCID 59022987, compound

HRID 1921763Notes

Reaction equation

HRID 1921763 reaction equation
[Br:1][C:2]1[N:7]2[C:8]([CH3:11])=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[O:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(O)CCC>[Br:1][C:2]1[N:7]2[C:8]([CH3:11])=[CH:9][N:10]=[C:6]2[C:5]([NH:23][C:22]2[CH:21]=[CH:20][C:19]([N:16]3[CH2:17][CH2:18][O:13][CH2:14][CH2:15]3)=[CH:25][CH:24]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 81531DiisopropylethylamineHCID 59023059HCID 59023059, compound

Product 1

HCID 59022987HCID 59022987, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5,8-Dibromo-3-methylimidazo[1,2-a]pyrazine (270 mg, 0.93 mmol) and 4-morpholinoaniline (200 mg, 1.1 mmol) are combined in nBuOH (10 mL) and DIPEA (240 μL, 1.4 mmol) is added. The mixture is heated at reflux for 10 h, cooled and the solvent removed under reduced pressure. The residue is purified by silica chromatography, eluting with 12%-100% EtOAc in cyclohexane, to afford the title compound as a red-brown solid (190 mg).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 10 h
  3. temperaturecooled
  4. customthe solvent removed under reduced pressure
  5. customThe residue is purified by silica chromatography
  6. washeluting with 12%-100% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-9b6323ed6bd1408ea3a6692aef61b5d4
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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