Dabco → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-amine

HRID 1921781

Reaction equation

HRID 1921781 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.N12CCN(CC1)CC2.[CH3:20][N:21]1[CH2:26][CH2:25][CH:24]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:23][CH2:22]1>C(O)(C)C>[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:35][C:32]2[CH:31]=[CH:30][C:29]([O:28][CH2:27][CH:24]3[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]3)=[CH:34][CH:33]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 115647984-((1-Methyl-4-piperidinyl)methoxy)benzenamineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 59023106(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(1-methyl-piperidin-4-ylmethoxy)-phenyl]-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5,8-dibromo-imidazo[1,2-a]pyrazine (0.100 g, 0.36 mmol) in isopropanol (5 mL) are added 1,4-diazabicyclo[2,2,2]octane (DABCO) (0.036 mL, 0.36 mmol) and 4-(1-methyl-piperidin-4-ylmethoxy)-phenylamine (79.6 mg, 0.36 mmol). The reaction mixture is stirred at 90° C. overnight. The solvent is evaporated and the residue chromatographed on silica gel column eluting with 97:3 followed by 94:6 and 90:10 DCM:MeOH. The title compound is obtained as a solid (20 mg, 13%). LCMS: Rt 2.30 min (94%), m/z (APCI) 417.

Workup

  1. customThe solvent is evaporated
  2. customthe residue chromatographed on silica gel column
  3. washeluting with 97:3

Sources & evidence

ORD record
ord-e3b8de7b6dbb45e09e7c471d0220aa6e
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Linked notes

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