Sodium Hydroxide → HCID 178525786, Verbindung

HRID 931265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 931265
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:28][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([O:26]C)=[O:25])[CH2:19]5)=[CH:16][CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[N:9]=[C:8]([C:10]3[NH:28][C:13]4=[N:14][C:15]([N:18]5[CH2:23][CH2:22][CH2:21][C@@H:20]([C:24]([OH:26])=[O:25])[CH2:19]5)=[CH:16][CH:17]=[C:12]4[N:11]=3)[CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 178501301HCID 178501301, Verbindung

Produkt 1

HCID 178525786HCID 178525786, VerbindungAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-methyl 1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylate (250 mg, 0.66 mmol) in ethanol (10 mL), was added an aqueous solution of sodium hydroxide (1N, 5 mL). The reaction mixture was stirred at room temperature for 2 h. The solvent was distilled off and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified with aqueous hydrochloric acid (10%) to pH˜2. The resulting precipitate was collected by filtration and dried under vacuum to afford (R)-1-(2-(2-cyclopropylpyrimidin-4-yl)-3H-imidazo[4,5-b]pyridin-5-yl)piperidine-3-carboxylic acid (200 mg). MS (ES+APCI) (M+H) 365.2

Aufarbeitung

  1. distillationThe solvent was distilled off
  2. customthe residue was partitioned between water and ethyl acetate
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0d2086e35c5f46af80477352893fa30f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296745B2

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