1-Chloro-4-methylphthalazine → 5-Amino-1-phenylbenzimidazole

HRID 1471339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471339
ClC1C2C(=CC=CC=2)C(C)=NN=1.[NH2:13][C:14]1[CH:34]=[CH:33][C:17]2[N:18]([C:21]3[CH:26]=[CH:25][C:24](C4C=CC=CC=4)=[CH:23][CH:22]=3)[CH:19]=[N:20][C:16]=2[CH:15]=1>CC(O)C>[NH2:13][C:14]1[CH:34]=[CH:33][C:17]2[N:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:19]=[N:20][C:16]=2[CH:15]=1

Komponenten

4

Edukt 2

HCID 2697331-Chloro-4-methylphthalazineHCID 13024894HCID 13024894, Verbindung

Produkt 1

HCID 9653125-Amino-1-phenylbenzimidazoleAusbeute 181,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-4-methylphthalazine (25 mg, 0.14 mmol) and 5-amino-1-(biphen-4-yl)benzimidazole (3) (28.5 mg, 0.10 mmol) in i-PrOH (2 mL) is stirred at 95° C. under argon for 2.5 h, cooled to room temperature, and concentrated at reduced pressure. The residue is diluted with sat. NaHCO3 (15 mL) and extracted with CHCl3 (60 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (3.2% to 4.8% methanol/ethyl acetate) to give 38 mg (88%) of 4 (BI-3039) as a light-brown solid, mp 272-274° C. IR 3339, 2979, 1522, 1412 cm−1; 1H NMR (CD3OD/CDCl3) δ 2.82 (s, 3H, CH3), 7.36-7.53 (m, 3H, PhH), 7.62 (d, J=9.00 Hz, 1H, 7-BenzimidH), 7.69 (m, 2H, Aril, 2H PhH), 7.79 (d, J=8.7 Hz, 1H, 6-BenzimidH), 7.86 (d, J=8.1 Hz, 2H, ArH), 7.91-7.98 (m, 2H, 6,7-PhthH), 8.07 (m, 1H, 5-PhthH), 8.10 (s, 1H, 4-BenzimidH), 8.32 (s, 1H, 2-BenzimidH), 8.45 ppm (m, 1H, 8-PhthH).

Aufarbeitung

  1. concentrationconcentrated at reduced pressure
  2. additionThe residue is diluted with sat. NaHCO3 (15 mL)
  3. extractionextracted with CHCl3 (60 mL)
  4. washThe extract is washed (brine)
  5. customdried
  6. customAfter solvent removal at reduced pressure
  7. customthe residue is purified on silica gel (3.2% to 4.8% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a243f4a8db75461eba0da2f8152b8a0e
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012217B2

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