Diisopropylethylamine → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-isopropylpiperidin-4-yl)-phenyl]amine

HRID 1924976Notes

Reaction equation

HRID 1924976 reaction equation
C(N(CC)C(C)C)(C)C.[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1)([CH3:12])[CH3:11].[Br:26][C:27]1[N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[C:30](Br)=[N:29][CH:28]=1>CC(O)C>[Br:26][C:27]1[N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[C:30]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([CH:16]3[CH2:15][CH2:14][N:13]([CH:10]([CH3:12])[CH3:11])[CH2:18][CH2:17]3)=[CH:24][CH:23]=2)=[N:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazineHCID 575900714-(1-Isopropylpiperidin-4-yl)aniline

Product 1

HCID 59023125(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-isopropylpiperidin-4-yl)-phenyl]amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N,N-Diisopropylethylamine (360 μL, 2.2 mmol) is added to a mixture of 4-(1-isopropylpiperidin-4-yl)phenylamine (220 mg, 1.0 mmol) and 5,8-dibromoimidazo[1,2-a]pyrazine (280 mg, 1.0 mmol) in iPrOH (5 mL) and heated at reflux for 48 h. The mixture is cooled and the solvent evaporated under reduced pressure to afford an orange-brown solid. This is partitioned between DCM (50 mL) and water (20 mL) and the layers are separated. The organic phase is washed with citric acid (10% aq., 3×25 mL). The combined washings are extracted with DCM (25 mL) and then made basic by addition of NaHCO3 (s). The mixture is extracted with DCM (3×25 mL) and the combined extracts dried over MgSO4 and evaporated. The material is used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. temperatureThe mixture is cooled
  4. customthe solvent evaporated under reduced pressure
  5. customto afford an orange-brown solid
  6. customThis is partitioned between DCM (50 mL) and water (20 mL)
  7. customthe layers are separated
  8. washThe organic phase is washed with citric acid (10% aq., 3×25 mL)
  9. extractionThe combined washings are extracted with DCM (25 mL)
  10. additionmade basic by addition of NaHCO3 (s)
  11. extractionThe mixture is extracted with DCM (3×25 mL)
  12. dry with materialthe combined extracts dried over MgSO4
  13. customevaporated
  14. customThe material is used without further purification

Sources & evidence

ORD record
ord-1e537b74c046411b9411fcad43e636be
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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