Hydrogen Bromide → HCID 67213086, compound

HRID 2223828Notes

Reaction equation

HRID 2223828 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([NH:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([O:24]C)=[CH:22][CH:23]=3)[N:13]=[C:12]([NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:11]=2)=[CH:5][CH:4]=1.C(O)(=O)C.Br.Br.C(OC(=O)C)C.Cl>C(OCC)(=O)C>[ClH:1].[NH:26]([C:12]1[N:11]=[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=2)[N:15]=[C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](=[O:24])[NH:20][CH:19]=2)[N:13]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 21866389Hydrogen chloride-ethyl acetateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 67213161HCID 67213161, compound

Product 1

HCID 67213086HCID 67213086, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A 565 mg portion of the N-(4-fluorophenyl)-N′-[(6-methoxypyridin-3-yl)methyl]-N″-phenyl-1,3,5-triazine-2,4,6-triamine hydrochloride synthesized in Invention Example 753 was mixed with 5 ml of 25% hydrobromic acid acetic acid solution and 1 ml of 48% hydrobromic acid aqueous solution and stirred at 80° C. for 6 hours. After evaporation of the reaction solution under a reduced pressure, the residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried using anhydrous magnesium sulfate. The solvent was evaporated under a reduced pressure, and the thus obtained residue was applied to a silica gel column chromatography and eluted with chloroform:methanol (99:1) to obtain a crude product. This crude product was dissolved in ethyl acetate and mixed with 4 M hydrochloric acid ethyl acetate solution, and the thus formed crystals were collected by filtration and dried to obtain 195 mg of 5-[({4-anilino-6-[(4-fluorophenyl)amino]-1,3,5-triazin-2-yl}amino)methyl]pyridine-2(1H)-one hydrochloride as colorless crystals.

Workup

  1. customAfter evaporation of the reaction solution under a reduced pressure
  2. additionthe residue was mixed with ethyl acetate and sodium bicarbonate aqueous solution in that order
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. customdried
  6. customThe solvent was evaporated under a reduced pressure
  7. washeluted with chloroform:methanol (99:1)
  8. customto obtain a crude product
  9. filtrationthe thus formed crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-acbdd8c7cf4143fda467d582e6c3a19e
Source dataset
uspto-grants-2008_05
Patent number
US07375222B2

Reaction notes

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