Ammonium Chloride → Tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate

HRID 1620043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1620043
[Cl-].[NH4+].CC[N:5]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[C:34]([O:38][C:39]([NH:41][C@H:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C@H:43]1[NH:48][C:49]1[C:57]([F:58])=[CH:56][C:52]([C:53](O)=[O:54])=[C:51]([Cl:59])[N:50]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(OCC)(=O)C.O.CN(C=O)C>[NH2:5][C:53]([C:52]1[CH:56]=[C:57]([F:58])[C:49]([NH:48][C@H:43]2[CH2:44][CH2:45][CH2:46][CH2:47][C@H:42]2[NH:41][C:39](=[O:40])[O:38][C:34]([CH3:35])([CH3:36])[CH3:37])=[N:50][C:51]=1[Cl:59])=[O:54]

Komponenten

9

Edukt 5

HCID 25517Ammonium Chloride2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866838426-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid

Produkt 1

HCID 86683847Tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamateAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ammonium chloride (1.10 g), WSC.HCl (2.97 g), HOBt.H2O (2.37 g), and diisopropylethylamine (7.06 ml) were added to a DMF solution (40 ml) containing 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid (2.00 g), followed by stirring at room temperature for 7 hours. A saturated aqueous ammonium chloride solution, water, and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether was added to the obtained residue, solid matter was collected by filtration, and a white solid of tert-butyl cis-2-(5-aminocarbonyl-6-chloro-3-fluoropyridin-2-ylamino)cyclohexylcarbamate (1.75 g) was thus obtained.

Aufarbeitung

  1. customThe organic layer was collected
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionDiisopropylether was added to the obtained residue, solid matter
  6. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-302cfc7e9a584c98be33a95d3af168fe
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772320B2

Notizen zur Reaktion

Wird geladen…