4-Amino-3,5-dichlorobenzotrifluoride → 4-[[4-[2,6-Dichloro-4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]benzonitrile

HRID 2305424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305424
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:8]=1)(=O)=O.[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([Cl:35])[C:26]=1[NH2:36]>O1CCOCC1>[Cl:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[C:27]([Cl:35])[C:26]=1[NH:36][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[N:8]=1

Komponenten

4

Edukt 2

HCID 1410944-Amino-3,5-dichlorobenzotrifluorideHCID 223984512-[(4-Cyanophenyl)amino]4-pyrimidinyl trifluoromethanesulfonate

Produkt 1

HCID 4887744-[[4-[2,6-Dichloro-4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]benzonitrileAusbeute 9,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

2-[(4-cyanophenyl)amino]-4-pyrimidinyl trifluoromethanesulfonate (0.0022 mol) and 2,6-dichloro-4-(trifluoromethyl)-benzenamine (0.0044 mol) were combined in 1,4-dioxane (2.5 ml) and heated in a sealed tube under Ar at 170° C. for 40 hours. The reaction mixture was allowed to cool to room temperature. Silica gel was added, and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH:NH4OH 100:0:0 to 97:2.7:0.3). The desired fractions were collected and the solvent was evaporated. The residue was recrystallized from CH3CN, filtered off and dried, yielding 0.086 g (9.2%) of 4-[[4-[[2,6-dichloro-4-(trifluoromethyl)-phenyl ]amino]-2-pyrimidinyl]amino]benzonitrile (compound 66).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. additionSilica gel was added
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash column chromatography over silica gel (eluent gradient: CH2Cl2:CH3OH:NH4OH 100:0:0 to 97:2.7:0.3)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated
  7. customThe residue was recrystallized from CH3CN
  8. filtrationfiltered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c171c555fb514c63893acf4f02f7dbf5
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06440986B2

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