Hydrochloric Acid → HCID 178497105, Verbindung

HRID 230023

Reaktionsgleichung

Reaktionsgleichung von HRID 230023
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:25]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[CH3:38][NH:39][C:40]1[C:41]([NH2:46])=[CH:42][CH:43]=[CH:44][CH:45]=1.Cl>ClCCl.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:38]2[N:46]([CH3:25])[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 78498N-Methyl-o-phenylenediamineHCID 81531Diisopropylethylamine2×HCID 178497106HCID 178497106, Verbindung

Produkt 1

HCID 178497105HCID 178497105, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2723924Mercury bis(trifluoroacetate)KatalysatorHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of methyl 1-[(trans-4-tert-butylcyclohexyl)amino]indane-5-carboxylate (0.43 g, 1.30 mmol) and DIEA (0.27 mL, 1.56 mmol) in dry dichloromethane (20 mL) was added thiophosgene (0.11 mL, 1.36 mmol) slowly. After stirring at 0° C. for 10 min and then at room temperature for 45 min, a solution of N-methylbenzene-1,2-diamine (0.38 g, 3.12 mmol) and DIEA (0.53 mL, 3.12 mmol) in dry dichloromethane (5 mL) was added. The reaction mixture was stirred for 1 h at room temperature, then diluted with dichloromethane (30 mL) and poured into aqueous HCl (1N, 30 mL). The organic layer was separated and washed with aqueous HCl (1N, 30 mL), saturated aqueous NaHCO3 (30 mL), brine (30 mL), dried over Na2SO4 and then concentrated to dryness. The residue was dissolved in dichloromethane (30 mL) and mercury (II) trifluoroacetate (0.61 g, 1.43 mmol) was added. The reaction mixture was stirred for 30 min at room temperature and then filtered through Celite. The organic solution was washed once with saturated NaHCO3 (30 mL), dried over Na2SO4 and concentrated. Chromatography (15% EtOAc in Hexane) afforded methyl 1-[(trans-4-tert-butylcyclohexyl)(1-methyl-1H-benzimidazol-2-yl)amino]indane-5-carboxylate. HPLC/MS: m/z=460.3 (M+1), Rt=3.46 min. 1H NMR (CDCl3): δ 7.85 (1H, s), 7.78 (1H, d, J=8.0 Hz), 7.71 (1H, m), 7.27 (1H, d, J=8.5 Hz), 7.25-7.18 (3H, m), 5.04 (1H, dd, J=7.5, 5.0 Hz), 3.90 (3H, s), 3.48 (3H, s), 3.24 (1H, m), 3.10 (1H, m), 2.83 (1H,

Aufarbeitung

  1. waitat room temperature for 45 min
  2. stirringThe reaction mixture was stirred for 1 h at room temperature
  3. customThe organic layer was separated
  4. washwashed with aqueous HCl (1N, 30 mL), saturated aqueous NaHCO3 (30 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. dissolutionThe residue was dissolved in dichloromethane (30 mL)
  8. stirringThe reaction mixture was stirred for 30 min at room temperature
  9. filtrationfiltered through Celite
  10. washThe organic solution was washed once with saturated NaHCO3 (30 mL)
  11. dry with materialdried over Na2SO4
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-994980470a7e40609f6fc8b6085c9a9b
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563815B2

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