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

HRID 1921753Notes

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

Participants

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

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