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Ammonium Chloride → Tert-butyl cis-2-(6-chloro-3-fluoro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate

HRID 1620035
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1620035
[C:1]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:33]([O:37][C:38]([NH:40][C@H:41]1[CH2:46][CH2:45][CH2:44][CH2:43][C@H:42]1[NH:47][C:48]1[C:56]([F:57])=[CH:55][C:51]([C:52](O)=[O:53])=[C:50]([Cl:58])[N:49]=1)=[O:39])([CH3:36])([CH3:35])[CH3:34].[Cl-].[NH4+]>C(OCC)(=O)C.CN(C=O)C.O>[Cl:58][C:50]1[N:49]=[C:48]([NH:47][C@H:42]2[CH2:43][CH2:44][CH2:45][CH2:46][C@H:41]2[NH:40][C:38](=[O:39])[O:37][C:33]([CH3:36])([CH3:34])[CH3:35])[C:56]([F:57])=[CH:55][C:51]=1[C:52]([NH:10][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2])=[O:53]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 25517Ammonium ChlorideHCID 68509CumylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866838426-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid

Produkt 1

HCID 86683841
Tert-butyl cis-2-(6-chloro-3-fluoro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cumylamine (1.97 ml), WSC.HCl (2.62 g), and HOBt.H2O (2.10 g) were added to a DMF (60 ml) solution containing 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-2-chloro-5-fluoronicotinic acid obtained in the 1st step, followed by stirring at room temperature for 4 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. The organic layer was collected, washed with a saturated aqueous sodium hydrogen carbonate solution and then with saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether and hexane were added to the obtained residue, solid matter was collected by filtration, and a white solid of tert-butyl cis-2-(6-chloro-3-fluoro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (4.41 g) was thus obtained.

Aufarbeitung

  1. customobtained in the 1st step
  2. customThe organic layer was collected
  3. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialwith saturated saline, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionDiisopropylether and hexane were added to the obtained residue, solid matter
  7. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-fa21bf6621e946d38a9d8249b8271fb6
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08772320B2

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