2-Pyridinemethanamine → 2-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-[(2-pyridinylmethyl)amino]-3,5-pyridinedicarbonitrile

HRID 885663Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:19]=[CH:18][C:13]3[O:14][CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4](SC2C=CC=CC=2)[N:3]=1.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][NH2:36]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:19]=[CH:18][C:13]3[O:14][CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([NH:36][CH2:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

100 mg (0.26 mmol) of 2-amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(phenyl-sulfanyl)-3,5-pyridinedicarbonitrile and 56 mg (0.52 mmol) of 2-picolylamine in 8 ml of DMF are heated at 100° C. After 3 hours, another 224 mg (2.08 mmol) of 2-picolylamine are added, and the mixture is heated at 100° C. for another 4 hours. After dilution with water, the mixture is extracted three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The evaporation residue is purified by preparative HPLC on reversed-phase silica gel.

Workup

extractionAfter dilution with water, the mixture is extracted three times with ethyl acetate
washThe combined organic phases are washed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe evaporation residue is purified by preparative HPLC on reversed-phase silica gel

Sources & evidence

ORD record: ord-53b686735e914e9292cce8e29581d9b8
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242281B2

Reaction notes

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