Dimethylformamide → 2-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-[(3-pyridinylmethyl)amino]-3,5-pyridinedicarbonitrile
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]=[C:31]([CH2:35]N)[CH:30]=1.C[N:38](C=O)C>>[NH2:38][C:4]1[C:5]([C:20]#[N:21])=[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:7]([C:8]#[N:9])=[C:2]([NH:1][CH2:35][C:31]2[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=2)[N:3]=1Participants
4
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 3-picolylamine in 8 ml of DMF are heated at 100° C. After 3 hours, another 224 mg (2.08 mmol) of 3-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 concentration 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 concentration residue is purified by preparative HPLC on reversed-phase silica gel
Sources & evidence
- ORD record
- ord-85886638a05a42edaf850792197cbba2
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242281B2
Reaction notes
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