Hydrochloric Acid → 1-[4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-chloro-pyrimidin-2-yl]-piperidine-4-carboxylic acid ethyl ester

HRID 409450Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409450
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([N:18]3[CH2:22][C@@H:21]([N:23]([CH2:41][C:42]4[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[C:44]([C:52]([F:55])([F:54])[F:53])[CH:43]=4)[C:24]4[N:29]=[CH:28][C:27]([C:30]5[CH:31]=[N:32][N:33](C6CCCCO6)[CH:34]=5)=[CH:26][N:25]=4)[CH2:20][C@H:19]3[CH2:56][CH3:57])[C:15]([Cl:58])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.CO.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[C:16]([N:18]3[CH2:22][C@@H:21]([N:23]([CH2:41][C:42]4[CH:47]=[C:46]([C:48]([F:49])([F:51])[F:50])[CH:45]=[C:44]([C:52]([F:54])([F:55])[F:53])[CH:43]=4)[C:24]4[N:25]=[CH:26][C:27]([C:30]5[CH:34]=[N:33][NH:32][CH:31]=5)=[CH:28][N:29]=4)[CH2:20][C@H:19]3[CH2:56][CH3:57])[C:15]([Cl:58])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 596143501-{4-[(2R,4S)-4-((3,5-bis-trifluoromethyl-benzyl)-{5-[1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}amino)-2-ethyl-pyrrolidin-1-yl]-5-chloro-pyrimidin-2-yl}-piperidine-4-carboxylic acid ethyl ester

Produkt 1

HCID 866483941-[4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-chloro-pyrimidin-2-yl]-piperidine-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 25 ml round-bottom flask was charged with 1-{4-[(2R,4S)-4-((3,5-bis-trifluoromethyl-benzyl)-{5-[1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-pyrimidin-2-yl}amino)-2-ethyl-pyrrolidin-1-yl]-5-chloro-pyrimidin-2-yl}-piperidine-4-carboxylic acid ethyl ester (70 mg, 0.084 mmol), 1N HCl (0.8 ml, 0.8 mmol) and MeOH (2 ml). The mixture is then heated to 60 degree for 30 minutes. After cooling down to rt, Saturated NaHCO3 and dichloromethane are added, then organic layer is collected. Removal of solvent give 1-[4-((2R,4S)-4-{(3,5-bis-trifluoromethyl-benzyl)-[5-(1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-2-ethyl-pyrrolidin-1-yl)-5-chloro-pyrimidin-2-yl]-piperidine-4-carboxylic acid ethyl ester and it is used for the next step without further purification.

Aufarbeitung

  1. temperatureThe mixture is then heated to 60 degree for 30 minutes
  2. customorganic layer is collected
  3. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-a8c47d2532534dfcb6cba876fbb1b882
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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