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

HRID 1924946

Reaction equation

HRID 1924946 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.[F: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>[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]([F:12])[CH:14]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27830553-Fluoro-4-(4-methylpiperazin-1-yl)anilineHCID 534859495,8-Dibromoimidazo[1,2-a]pyrazine

Product 1

HCID 59023046(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[3-fluoro-4-(4-methyl-piperazin-1-yl)-phenyl]-amineYield 5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Following the general procedure for amine displacement using 5,8-dibromoimidazo[1,2-a]pyrazine (0.50 g, 1.81 mmol), 3-fluoro-4-(4-methyl-piperazin-1-yl)-phenylamine (0.45 g, 2.17 mmol) and DIPEA (0.47 mL, 2.72 mmol) in iPrOH (5 mL). The crude material is purified by silica gel column chromatography eluting with 90:10 DCM:MeOH to give the title compound (35 mg, 5%).

Workup

  1. customThe crude material is purified by silica gel column chromatography
  2. washeluting with 90:10 DCM

Sources & evidence

ORD record
ord-cb5532ca82cd427c90fca82602e04e02
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Linked notes

Loading…