p-Toluenesulfonic acid monohydrate → HCID 117861219, compound

HRID 2284710Notes

Reaction equation

HRID 2284710 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=3[OH:31])=O)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH3:18])[C:12]([C:19]3[O:31][C:23]4[CH:24]=[C:25]([N+:28]([O-:30])=[O:29])[CH:26]=[CH:27][C:22]=4[N:21]=3)=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117856879HCID 117856879, compound

Product 1

HCID 117861219HCID 117861219, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
155 °C

Procedure

To 2-((3-fluorophenyl)amino)-N-(2-hydroxy-4-nitrophenyl)-4-(propylamino)pyrimidine-5-carboxamide (E24, 11 mg) and p-toluenesulfonic acid monohydrate (15 mg), xylene (1.5 mL) was added at room temperature, and the mixture was stirred at 155° C. for 4 hours. The reaction mixture was cooled to room temperature, and then purified by silica gel column chromatography (eluent, 100 to 80% ethyl acetate in methanol). To the obtained solid matter, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the obtained residue, ethyl acetate were added, and the solid matter was taken by filtration to obtain N2-(3-fluorophenyl)-5-(6-nitrobenzo[d]oxazol-2-yl)-N4-propylpyrimidine-2,4-diamine (E25) as yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified by silica gel column chromatography (eluent, 100 to 80% ethyl acetate in methanol)
  3. additionTo the obtained solid matter, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added
  4. customThe organic layer was separated
  5. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. additionTo the obtained residue, ethyl acetate were added
  9. filtrationthe solid matter was taken by filtration

Sources & evidence

ORD record
ord-00ee17252ca24ebaae9617fc2740063e
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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