Diisopropylethylamine → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-chloro-4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1921765

Reaction equation

HRID 1921765 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.[Cl:12][C:13]1[CH:14]=[C:15]([NH2:26])[CH:16]=[CH:17][C:18]=1[N:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>CC(O)C>[NH3:4].[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:26][C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[C:13]([Cl:12])[CH:14]=2)=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 8203433-Chloro-4-(4-methylpiperazin-1-yl)anilineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Product 2

HCID 222AmmoniaHCID 59023078(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-chloro-4-(4-methyl-piperazin-1-yl)-phenyl]-amineYield 39.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Following the general procedure for amine displacement using 5,8-dibromoimidazo[1,2-a]pyrazine (0.20 g, 0.72 mmol), 3-chloro-4-(4-methyl-piperazin-1-yl)-phenylamine (0.263 g, 1.08 mmol) and DIPEA (0.19 mL, 1.08 mmol) in iPrOH (5 mL). Purification of the crude compound by silica gel column chromatography, eluting with 95:5 DCM:NH3 (7M in MeOH), affords the title compound (60 mg, 20%).

Workup

  1. customPurification of the crude compound by silica gel column chromatography
  2. washeluting with 95:5 DCM

Sources & evidence

ORD record
ord-215de1a3f8f5476fbfe45a06ee196bd7
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Linked notes

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