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

HRID 1924981Notes

Reaction equation

HRID 1924981 reaction equation
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5](Br)=[N:4][CH:3]=1.[CH:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)([CH3:14])[CH3:13].C(N(C(C)C)CC)(C)C>>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:27][C:24]2[CH:23]=[CH:22][C:21]([N:18]3[CH2:17][CH2:16][N:15]([CH:12]([CH3:14])[CH3:13])[CH2:20][CH2:19]3)=[CH:26][CH:25]=2)=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 91615454-[4-(Propan-2-yl)piperazin-1-yl]anilineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 59022995(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amineYield 43.1%

Procedure

A solution of 5,8-dibromo-imidazo[1,2-a]pyrazine (0.134 g, 0.48 mmol), 4-(4-isopropyl-piperazin-1-yl)-phenylamine (0.118 g, 0.54 mmol) and diisopropylethylamine (0.093 mL, 0.54 mmol) is stirred at 90° C. for 18 hours. The reaction mixture is concentrated in vacuo and partitioned between DCM and sat. NaHCO3. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with 98:2 DCM:MeOH to afford the title compound (0.086 g, 43%).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. custompartitioned between DCM and sat. NaHCO3
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with 98:2 DCM

Sources & evidence

ORD record
ord-dc0d4cc422ea42f19d9351a655e67dae
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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