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Hydrochloric Acid → (S)-N-(7-(2-(1-amino-2-(3,5-difluorophenyl)ethyl)-6-chloropyridin-3-yl)-4-chloro-1-methyl-1H-indazol-3-yl)methanesulfonamide

HRID 2170402
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2170402
[Cl:1][C:2]1[N:7]=[C:6]([C@@H:8]([NH:18]C(=O)C(F)(F)F)[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)[C:5]([C:25]2[CH:26]=[CH:27][C:28]([Cl:40])=[C:29]3[C:33]=2[N:32]([CH3:34])[N:31]=[C:30]3[NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[CH:4][CH:3]=1.[Li+].[OH-].Cl>CCO>[NH2:18][C@H:8]([C:6]1[C:5]([C:25]2[CH:26]=[CH:27][C:28]([Cl:40])=[C:29]3[C:33]=2[N:32]([CH3:34])[N:31]=[C:30]3[NH:35][S:36]([CH3:39])(=[O:37])=[O:38])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[CH2:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 90281429(S)-N-(1-(6-chloro-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2,2,2-trifluoroacetamide

Produkt 1

HCID 90281213(S)-N-(7-(2-(1-amino-2-(3,5-difluorophenyl)ethyl)-6-chloropyridin-3-yl)-4-chloro-1-methyl-1H-indazol-3-yl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of (S)—N-(1-(6-chloro-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2,2,2-trifluoroacetamide (57D, 870 mg, 1.40 mmol) in EtOH (16 mL) was added 2M aqueous LiOH (7.0 mL, 13.98 mmol). The reaction was heated in a microwave reactor at 130° C. for 10 minutes. Upon cooling, the reaction mixture was acidified with 2N aqueous HCl until at pH 5. The reaction mixture was then concentrated in vacuo and taken in EtOAc. To the solution was added saturated aqueous NaHCO3 until the aqueous layer was at pH 10. The organic layer was collected, and the aqueous layer was extracted an additional time with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo, and used without further purification. MS (m/z) 526.06 [M+H]+.

Aufarbeitung

  1. temperatureUpon cooling
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additionTo the solution was added saturated aqueous NaHCO3 until the aqueous layer
  4. customThe organic layer was collected
  5. extractionthe aqueous layer was extracted an additional time with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customused without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8ffe87717439431f8e9afcbd0894a979
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09050344B2

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