Ethylenediamine → HCID 57833434, compound

HRID 729921Notes

Reaction equation

HRID 729921 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:23]=[CH:22][C:12]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]#[N:21])[CH:15]=3)=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[CH2:30](N)[CH2:31][NH2:32].[S]>CN(C=O)C>[NH:21]1[CH2:30][CH2:31][N:32]=[C:20]1[C:16]1[CH:15]=[C:14]([O:13][C:12]2[CH:22]=[CH:23][C:9]([NH:8][C:6]3[CH:5]=[C:4]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:3]=[C:2]([NH2:1])[N:7]=3)=[CH:10][CH:11]=2)[CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 57833365HCID 57833365, compound

Product 1

HCID 57833434HCID 57833434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-{4-[(2-amino-6-phenylpyrimidin-4-yl)amino]phenoxy}pyridine-2-carbonitrile (0.2 g, 0.53 mmol, prepared in Example 8), ethylene diamine (0.095 g, 1.58 mmol), and sulfur (0.05 g, 1.58 mmol) in DMF (3 mL) was heated at 80° C. for 3 days. The solvent was then removed by evaporation under reduced pressure. The residue was purified by preparative HPLC followed by preparative TLC (EtOAc:NH4OH=99:2) to afford pure product, 0.01 g (5%). 1H NMR (DMSO-d6) δ 9.39 (s, 1H), 8.41 (d, 1H), 7.84 (m, 4H), 7.42 (m, 3H), 7.37 (d, 1H), 7.09 (m, 3H), 6.95 (s, 1H), 6.46 (s, 1H), 6.37 (s, 2H); MS ES 424 (M+H)+ calc 424.

Workup

  1. customThe solvent was then removed by evaporation under reduced pressure
  2. customThe residue was purified by preparative HPLC
  3. customto afford pure product, 0.01 g (5%)

Sources & evidence

ORD record
ord-61a408f71a3e4bcdafe5e8f6dcf7c156
Source dataset
uspto-grants-2009_09
Patent number
US07582645B2

Reaction notes

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