Thionyl Chloride → HCID 72203009, Verbindung

HRID 629060

Reaktionsgleichung

Reaktionsgleichung von HRID 629060
[N:1]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([OH:12])=O)[CH:4]=[N:3][CH:2]=1.O=S(Cl)Cl.[Cl:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>C(Cl)Cl>[Cl:20][C:21]([F:30])([F:31])[O:22][C:23]1[CH:24]=[CH:25][C:26]([NH:27][C:10](=[O:12])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([C:5]3[CH:4]=[N:3][CH:2]=[N:1][CH:6]=3)[CH:8]=2)=[CH:28][CH:29]=1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 5727934-(Chlorodifluoromethoxy)anilineHCID 41872503-Pyrimidin-5-yl-benzoic acid

Produkt 1

HCID 72203009HCID 72203009, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-pyrimidin-5-yl-benzoic acid (100 mg, 0.50 mmol) and SOCl2 (73 μL, 1.0 mmol) was heated under reflux for 4 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in DCM (5 mL) and slowly added to a mixture of 4-(chlorodifluoromethoxy)aniline (106 mg, 0.55 mmol) and TEA (140 μL, 1.0 mmol) in DCM (5 mL). The mixture was stirred at RT overnight. The solvent was evaporated off under reduced pressure and the residue was suspended in EtOAc (10 mL), filtered through a 10 μm Isolute® fritted cartridge and the filtrate was evaporated to dryness under reduced pressure to give the crude product which was purified by preparative HPLC to afford the title compound. LC-MS (Condition 4) tR=1.15 min, m/z=375.8 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.40 (d, J=9.05 Hz, 2H) 7.73 (t, J=7.82 Hz, 1H) 7.92 (m, 2H) 8.06 (t, J=6.97 Hz, 2H) 8.37 (t, J=1.96 Hz, 1H) 9.24-9.29 (m, 3H) 10.52 (s, 1H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. customThe solvent was evaporated off under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (5 mL)
  5. customThe solvent was evaporated off under reduced pressure
  6. filtrationfiltered through a 10 μm Isolute® fritted cartridge
  7. customthe filtrate was evaporated to dryness under reduced pressure
  8. customto give the crude product which
  9. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5f532288e94142d7b3ae49ecd0ab211e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315489B2

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