Isopropanol → HCID 1386209, Verbindung

HRID 1471332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471332
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][N:3]=1.[CH2:18]([N:21]1[C:25]2[CH:26]=[CH:27][C:28]([NH2:30])=[CH:29][C:24]=2[N:23]=[CH:22]1)[C:19]#[CH:20].[CH3:31][CH:32](O)[CH3:33]>>[C:18]1([N:21]2[C:25]3[CH:26]=[CH:27][C:28]([NH:30][C:2]4[C:11]5[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=5)[C:5]([C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)=[N:4][N:3]=4)=[CH:29][C:24]=3[N:23]=[CH:22]2)[CH:33]=[CH:32][CH:31]=[CH:20][CH:19]=1

Komponenten

4

Edukt 3

HCID 3776IsopropanolHCID 2721091-Chloro-4-phenylphthalazineHCID 59372953HCID 59372953, Verbindung

Produkt 1

HCID 1386209HCID 1386209, VerbindungAusbeute 99 %

Versuchsvorschrift

A solution of 1-chloro-4-phenylphthalazine (81 mg, 0.34 mmol) and 1-(prop-2-ynyl)-5-aminobenzimidazole (3) (36 mg, 0.21 mmol) in i-PrOH (6 mL) is stirred at 95° C. under argon for 2 h and then concentrated. 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 (1% to 10% methanol/ethyl acetate) to give 78 mg (99%) of 5 (BI-3007) as a yellow solid, mp 227-229° C. IR 3304, 2965, 1495, 1401 cm−1; NMR (DMSO-d6) δ 3.54 (t, J=2.4 Hz, 1H, CH≡CCH2), 4.83 (bs, 2H, NH2), 5.24 (d, J=2.4 Hz, 2H, CH≡CCH2), 7.52-7.62 (m, 3H, PhH), 7.64 (d, J=8.7 Hz, 1H, 7-BenzimidH), 7.65-7.71 (m, 2H, PhH), 7.79 (dd, J=8.7, 1.8 Hz, 1H, 6-BenzimidH), 7.89 (d, J=8.1 Hz, 1H, 5-PhthH), 7.91-7.98 (m, 1H, 6-PhthH), 7.99-8.08 (m, 1H, 7-PhthH), 8.25 (s, 1H, 2-BenzimidH), 8.34 (d, J=1.8 Hz, 4-BenzimidH), 8.72 (d, J=8.1 Hz, 8-PhthH), 9.32 ppm (s, 1H, NH).

Aufarbeitung

  1. concentrationconcentrated
  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 (1% to 10% methanol/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8352324f9e144efcb722ac4928913a92
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012217B2

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