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

HRID 1784009Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-[5-(2-methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide (71.5 mg, 0.16 mmol) and pyridinium hydrochloride (91 mg, 0.79 mmol) in water (0.5 mL) in a sealed tube is heated at 150° C. for 25 minutes. After this time the solvent is removed in vacuo. The residue is chromatographed on silica gel, eluting with DCM followed by 98:2 and 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 yellow solid (34.5 mg, 49%).

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-c2f81362810d41deb825d38a2fa6e642
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501411B2

Reaction notes

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