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Pyridinium hydrochloride → 4-[5-(2-oxo-1,2-dihydropyridin-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]-N-pyridin-3ylmethyl benzamide

HRID 1921753
Notes
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Reaction equation

HRID 1921753 reaction equation
C([O:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]3[CH:16]=[CH:17][N:18]=[C:14]3[C:13]([NH:19][C:20]3[CH:35]=[CH:34][C:23]([C:24]([NH:26][CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:25])=[CH:22][CH:21]=3)=[N:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1)C.Cl.[NH+]1C=CC=CC=1>O>[O:3]=[C:4]1[CH:9]=[C:8]([C:10]2[N:15]3[CH:16]=[CH:17][N:18]=[C:14]3[C:13]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([C:24]([NH:26][CH2:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:25])=[CH:34][CH:35]=3)=[N:12][CH:11]=2)[CH:7]=[CH:6][NH:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 866167464-[5-(2-Ethoxypyridin-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl benzamide

Product 1

HCID 590229784-[5-(2-oxo-1,2-dihydropyridin-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]-N-pyridin-3ylmethyl benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-[5-(2-ethoxypyridin-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl benzamide (82 mg, 0.18 mmol) and pyridinium hydrochloride (101 mg, 0.88 mmol) in water (0.5 mL) is heated at 150° C. for 20 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 90:10 DCM:NH3 (7M in MeOH), and the fractions containing the desired product are combined and evaporated. The title compound is isolated as a solid. HPLC (254 nm): Rt 1.83 min (99.1%); m/z (APCI) 438 (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-0660711e3f0d4aa8aff8c3163eabb8cc
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173656B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes