Pyridinium hydrochloride → 4-{8-[4-(4-Methylpiperazin-1-yl)phenylamino]imidazo[1,2-a]pyrazin-5-yl}-1H-pyridin-2-one

HRID 1924897Notes

Reaction equation

HRID 1924897 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[C:16]4[N:17]([CH:30]=[CH:31][N:32]=4)[C:18]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([O:27]CC)[CH:22]=4)=[CH:19][N:20]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl.[NH+]1C=CC=CC=1>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[C:16]4[N:17]([CH:30]=[CH:31][N:32]=4)[C:18]([C:21]4[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=4)=[CH:19][N:20]=3)=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 59023089(4-(4-Methylpiperazin-1-yl)phenyl)-[5-(2-ethoxypyridin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]amine

Product 1

HCID 573940024-{8-[4-(4-Methylpiperazin-1-yl)phenylamino]imidazo[1,2-a]pyrazin-5-yl}-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (4-(4-methylpiperazin-1-yl)phenyl)-[5-(2-ethoxypyridin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]amine (103 mg, 0.24 mmol) and pyridinium hydrochloride (130 mg, 1.2 mmol) in water (0.2 mL) is heated at 150° C. for 25 minutes in a sealed tube. After this time the solvent is removed in vacuo. The residue is chromatographed on silica gel, eluting with DCM followed by 92:8 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated to afford the title compound as a solid. HPLC (254 nm): Rt 1.70 min (99.7%); m/z (APCI) 402 (M+H)+.

Workup

  1. customAfter this time the solvent is removed in vacuo
  2. customThe residue is chromatographed on silica gel
  3. washeluting with DCM
  4. additionNH3 (7M in MeOH), and the fractions containing the desired product
  5. customevaporated

Sources & evidence

ORD record
ord-85290e9dbec8484cb65be3b01f26587c
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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