Diisopropylethylamine → HCID 178423604, Verbindung

HRID 243279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243279
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([C@@H:11]([NH2:13])[CH3:12])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[C:21]1[N:29]=[CH:28][N:27]=[C:26]2[C:22]=1[N:23]=[CH:24][NH:25]2.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([C@@H:11]([NH:13][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][NH:25]4)[CH3:12])[N:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 68157022(S)-1-(4-Methyl-1-phenyl-1H-benzo[D]imidazol-2-YL)ethanamineHCID 178478393HCID 178478393, Verbindung

Produkt 1

HCID 178423604HCID 178423604, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (S)-1-(4-methyl-1-phenyl-1H-benzoimidazol-2-yl)ethylamine from Example 3 (100 mg, 0.398 mmol), 6-chloro-9H-purine (68 mg, 0.438 mmol) and DIPEA (83 μL, 0.478 mmol) in n-butanol (1 mL) was stirred in a sealed vial at 100° C. for 20 h. After cooling to RT, the mixture was partitioned between DCM and water. The organic layer was then separated, dried and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and then sonicated in cyclohexane affording 108 as an off-white solid (56 mg, 38%) LCMS: RT 3.17 min [M+H]+ 370.1. 1H NMR (DMSO, 400 MHz): δ 8.13 (1H, bs), 8.08 (1H, s), 7.96-7.85 (1H, m), 7.67-7.44 (5H, m), 7.12-6.99 (2H, m), 6.86 (1H, d, J=7.80 Hz), 5.49 (1H, br), 2.56 (3H, s), 1.57 (3H, d, J=6.86 Hz)

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. customthe mixture was partitioned between DCM and water
  3. customThe organic layer was then separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
  7. customsonicated in cyclohexane affording 108 as an off-white solid (56 mg, 38%) LCMS: RT 3.17 min [M+H]+ 370.1

Quellen und Nachweise

ORD-Eintrag
ord-37375efb4e864dff9a715a06b3d684f4
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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