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Hydrochloric Acid → (1S,2S)-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanecarboxylic acid

HRID 74952
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74952
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15](S(C)(=O)=O)[C:14]([F:21])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[NH2:32][C@H:33]1[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]1[C:39]([OH:41])=[O:40].C([O-])([O-])=O.[Na+].[Na+].CCN(C(C)C)C(C)C.[Li+].[OH-].Cl>C1COCC1.CC#N>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:32][C@H:33]4[CH2:38][CH2:37][CH2:36][CH2:35][C@@H:34]4[C:39]([OH:41])=[O:40])[C:14]([F:21])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 7128323(1S,2S)-2-Aminocyclohexanecarboxylic AcidHCID 672887915-Chloro-3-(5-fluoro-4-methylsulfonyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

Produkt

1
HCID 68007420(1S,2S)-2-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 5-chloro-3-(5-fluoro-4-methylsulfonyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 1a, (0.49 g, 1.05 mmol), (1S,2S)-2-amino-cyclohexanecarboxylic acid (0.30 g, 2.10 mmol), freshly ground Na2CO3 (0.22 g, 2.10 mmol), and iPr2NEt (0.37 mL, 2.10 mmol) in THF (10 mL) and CH3CN (2 mL) were heated in a sealed vessel to 130° C. for 30 minutes under microwave irradiation. The mixture was cooled to room temperature. A solution of 1N LiOH (3.1 mL, 3.1 mmol) was added and the mixture was stirred at 120° C. for 10 minutes under microwave irradiation. The mixture was acidified with 1N HCl until pH 2 under vigorous stirring. The newly formed solid was collected by vacuum filtration. The solid was washed with small amounts of water and EtOAc. The solid was dried in vacuo to provide the desired product.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe newly formed solid was collected by vacuum filtration
  3. washThe solid was washed with small amounts of water and EtOAc
  4. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6f06578ca15a4af2a2d7af656cace7bd
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829007B2

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