2-(Oxan-4-yl)ethan-1-amine → 5-(4-{[2-(Tetrahydropyran-4-yl)ethylamino]methyl}phenoxy)pyrazine-2-carboxamide

HRID 130876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 130876
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([NH2:16])=[O:15])=[N:12][CH:13]=2)=[CH:5][CH:4]=1)=O.[O:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][NH2:27])[CH2:21][CH2:20]1.[BH4-].[Na+]>CO>[O:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][NH:27][CH2:1][C:3]2[CH:18]=[CH:17][C:6]([O:7][C:8]3[N:9]=[CH:10][C:11]([C:14]([NH2:16])=[O:15])=[N:12][CH:13]=3)=[CH:5][CH:4]=2)[CH2:21][CH2:20]1

Komponenten

5

Edukt 3

HCID 27731982-(Oxan-4-yl)ethan-1-amineHCID 4311764Sodium borohydrideHCID 597301885-(4-Formylphenoxy)pyrazine-2-carboxamide

Produkt 1

HCID 597304155-(4-{[2-(Tetrahydropyran-4-yl)ethylamino]methyl}phenoxy)pyrazine-2-carboxamideAusbeute 37,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Place 5-(4-formylphenoxy)pyrazine-2-carboxamide (Example 437, Part B) (0.150 g, 0.617 mmol), 2-(tetrahydropyran-4-yl)ethylamine (0.0797 g, 0.617 mmol) and 3 Å molecular sieves in a vial. Add methanol (3.1 mL), cap and stir overnight. Add NaBH4 (in excess over two portions) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 5 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 10 g ISCO® column with 2.0 M NH3 in methanol and ethyl acetate. After concentrating, take the product up in dichloromethane (25 mL) and wash with 1.0 N NaOH solution (2×10 mL). Dry the organic layer over Na2SO4, filter and concentrate to give the title compound (0.0819 g, 37.2%): MS ES+ 357.1 (M+H)+, base peak 228.0 (M−C7H14NO)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 19 min], tR=7.4 min, 100% purity.

Aufarbeitung

  1. customDry the column in a vacuum oven at room temperature
  2. customPurify
  3. washby eluting through a 10 g ISCO® column with 2.0 M NH3 in methanol and ethyl acetate
  4. concentrationAfter concentrating
  5. washwash with 1.0 N NaOH solution (2×10 mL)
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-be9072b678da4fae9b9f41b9c36f4d89
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381719B2

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