p-Toluenesulfonic acid → HCID 71075523, compound

HRID 1028104Notes

Reaction equation

HRID 1028104 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Br:8])[CH:7]=1.Cl[C:14]1[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=1.CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Br:8][C:6]1[CH:5]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:3]=[C:2]([NH:1][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 67240182HCID 67240182, compound

Product 1

HCID 71075523HCID 71075523, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-amino-5-bromophenyl)acetamide (3.25 g, 14.19 mmol) and 2-chloro-4-(trifluoromethyl)pyrimidine (2.054 mL, 17.03 mmol) in dioxane (8.5 mL) under nitrogen, was added pTsOH (2.70 g, 14.19 mmol). The reaction was stirred at 100° C. for 18 h, cooled to at room temperature. Solvent was removed under reduced pressure and the resultant residue was diluted with sat. NaH-CO3 (aq) and DCM. The organic was dried over sodium sulfate and was concentrated to dryness. Purified by flash chromatography (1:1 to 0:100 hexanes:ethyl acetate) to yield N-(3-bromo-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)acetamide (2.71 g, 7.22 mmol, 51%) as a beige powder. MS APCI: [M+H]m/z 377.0.

Workup

  1. temperaturecooled to at room temperature
  2. customSolvent was removed under reduced pressure
  3. additionthe resultant residue was diluted with sat. NaH-CO3 (aq) and DCM
  4. dry with materialThe organic was dried over sodium sulfate
  5. concentrationwas concentrated to dryness
  6. customPurified by flash chromatography (1:1 to 0:100 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-2ff5bbf3b3f7497184d2f7ee204dd6f7
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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