5-Amino-1-phenylbenzimidazole → HCID 59373121, Verbindung

HRID 1471338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471338
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[N:4][N:3]=1.[NH2:17][C:18]1[CH:32]=[CH:31][C:21]2[N:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=[N:24][C:20]=2[CH:19]=1>CC(O)C>[C:25]1([N:22]2[C:21]3[CH:31]=[CH:32][C:18]([NH:17][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([CH2:12][O:13][CH2:14][C:15]#[CH:16])=[N:4][N:3]=4)=[CH:19][C:20]=3[N:24]=[CH:23]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 9653125-Amino-1-phenylbenzimidazoleHCID 59372952HCID 59372952, Verbindung

Produkt 1

HCID 59373121HCID 59373121, VerbindungAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-4-(prop-2-ynyloxy)methylphthalazine (3) (20 mg, 0.09 mmol) and 5-amino-1-phenylbenzimidazole (15 mg, 0.07 mmol) in i-PrOH (2 mL) is stirred at 95° C. under argon for 2.5 h. The reaction mixture is concentrated, quenched with sat. NaHCO3 (10 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 (0:1:2 to 1:25:0 methanol/ethyl acetate/hexane) to give 8 mg (27%) of BI-3035 as a light-brown solid, mp 89-91° C. IR 3321, 2927, 1496 cm−1; 1H NMR (CDCl3) δ 2.60 (t, J=2.4 Hz, 1H, CH≡C—CH2O), 4.98 (s, 2H, CH2), 5.36 (d, J=2.4 Hz, CH≡CCH2O), 6.94 (dd, J=8.7, 2.1 Hz, 1H, 6-BenzimidH), 7.27 (d, J=2.1 Hz, 1H, 4-BenzimidH), 7.41 (d, J=8.7 Hz, 1H, 7-BenzimidH), 7.41-7.63 (m, 5H, PhH), 7.90-8.02 (m, 2H, 6,7-PhthH), 8.06 (s, 1H, 2-BenzimidH), 8.14 (m, 1H, 5-PhthH), 8.35 (m, 1H, 8-PhthH).

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated
  2. customquenched with sat. NaHCO3 (10 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 (0:1:2 to 1:25:0 methanol/ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-75c31f9cac3947318e91b669617d3351
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012217B2

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