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

HRID 885663
Notes
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Reaction equation

HRID 885663 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 195092-Pyridinemethanamine2×HCID 179760052-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile

Product 1

HCID 574243172-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-[(2-pyridinylmethyl)amino]-3,5-pyridinedicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. extractionAfter dilution with water, the mixture is extracted three times with ethyl acetate
  2. washThe combined organic phases are washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes