Ethyl Acetate → Methyl 2-benzylamino-6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)nicotinate

HRID 340443

Reaktionsgleichung

Reaktionsgleichung von HRID 340443
C(N([CH:7]([CH3:9])[CH3:8])CC)(C)C.[C@@H:10]1([NH2:17])[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[NH2:16].[CH3:18]N1CCCC1=O.[CH2:25]([NH:32][C:33]1[N:42]=[C:41](Cl)[CH:40]=[CH:39][C:34]=1[C:35]([O:37][CH3:38])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:44]([O:47]CC)(=[O:46])C>O>[CH2:25]([NH:32][C:33]1[N:42]=[C:41]([NH:16][C@@H:11]2[CH2:12][CH2:13][CH2:14][CH2:15][C@@H:10]2[NH:17][C:44]([O:47][C:7]([CH3:9])([CH3:18])[CH3:8])=[O:46])[CH:40]=[CH:39][C:34]=1[C:35]([O:37][CH3:38])=[O:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

7

Edukt 5

HCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 3429171,2-Diaminocyclohexane, cis-HCID 86683851Methyl 2-benzylamino-6-chloronicotinate

Produkt 1

HCID 86683850Methyl 2-benzylamino-6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)nicotinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Diisopropylethylamine (7.5 ml) and cis-cyclohexane-1,2-diamine (5.0 g) were added to an N-methylpyrrolidone (50 ml) solution containing methyl 2-benzylamino-6-chloronicotinate (6.0 g), followed by stirring at 120° C. for 11 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was collected, washed with saturated saline, and dried over anhydrous sodium sulfate, and then the solvent was distilled away under reduced pressure. Di-tert-butyl dicarbonate (4.7 g) was added to a tetrahydrofuran (50 ml) solution containing the obtained residue and the resulting mixture was left at rest at room temperature for 3 days. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel:silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=3:1), and a light yellow solid of methyl 2-benzylamino-6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)nicotinate (7.7 g) was thus obtained.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was collected
  3. washwashed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionDi-tert-butyl dicarbonate (4.7 g) was added to a tetrahydrofuran (50 ml) solution
  7. additioncontaining the obtained residue
  8. waitthe resulting mixture was left at rest at room temperature for 3 days
  9. distillationThe solvent was distilled away under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (silica gel:silica gel 60 (spherical shape) (Kanto Chemical Co., Inc.); hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-efaecba711b74c7a9af3326002b88ba2
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895585B2

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