Ammonium Chloride → N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)acetamide

HRID 626497Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626497
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[NH4+].[Cl-]>CO.[Zn]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18](=[O:20])[CH3:19])[CH:12]=2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 90409856N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide

Produkt 1

HCID 90410482N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)acetamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)acetamide (1.48 g, 5.40 mmol) and NH4Cl (7.22 g, 135 mmol) in MeOH (25 mL) was treated with zinc (2.82 g, 43.2 mmol) and stirred at RT for 1 h. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to near-dryness. The residue was treated with water, extracted with EtOAc (2×) and the combined organics were washed with brined, dried over Na2SO4 and concentrated to dryness. The material was treated with 60% EtOAc/Hex, the solid collected via filtration, washed with 60% EtOAc/Hex and dried to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)acetamide (750 mg, 57%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.47 (s, 1H), 8.11 (d, J=5.7 Hz, 1H), 7.76 (d, J=2.9 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.24 (dd, J=8.9, 3.0 Hz, 1H), 6.59 (dd, J=5.7, 2.4 Hz, 1H), 6.49 (d, J=8.9 Hz, 1H), 6.00 (s, 2H), 2.01 (s, 3H); MS (ESI) m/z: 245.1 (M+H+).

Aufarbeitung

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with MeOH
  3. concentrationthe filtrate concentrated to near-dryness
  4. additionThe residue was treated with water
  5. extractionextracted with EtOAc (2×)
  6. washthe combined organics were washed with brined,
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. additionThe material was treated with 60% EtOAc/Hex
  10. filtrationthe solid collected via filtration
  11. washwashed with 60% EtOAc/Hex
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-27ed5f88f3eb4920a37b8d60b18baee7
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309224B2

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