Methanol → Methyl (6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazin-3-yl)carbamate

HRID 1714869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714869
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[N:16][C:15](C(O)=O)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.CCN(CC)CC.[CH3:51][OH:52].C[N:54]([CH:56]=[O:57])C>O>[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[N:17]=[N:16][C:15]([NH:54][C:56](=[O:57])[O:52][CH3:51])=[CH:14][CH:13]=2)[CH2:10][CH2:11]1

Komponenten

7

Edukt 5

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 462254266-(4-(2-(Trifluoromethyl)phenoxy)piperidin-1-yl)pyridazine-3-carboxylic acid

Produkt 1

HCID 23630218Methyl (6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazin-3-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxylic acid (150 mg, 0.4 mmol), DPPA (100 μL, 0.46 mmol) and Et3N (65 μL, 0.46 mmol) in DMF (1.5 mL) was stirred at r.t. overnight. MeOH (150 μL, 3.7 mmol) was then added and the mixture was heated at 65-70° C. for 6 h. After cooling, the mixture was diluted with water and extracted with EtOAc. The EtOAc extract was washed twice with water, dried (Na2SO4) and concentrated. CombiFlash chromatography (10 g, 40-80% EtOAc in hexanes in 20 min, 20 mL/min, 15 mL/fraction) gave the title compound as a white solid. 1H NMR (500 MHz, acetone-d6): δ 1.89-1.97 (m, 2H), 2.15 (m, 2H), 3.65-3.71 (m, 2H), 3.76 (s, 3H), 3.87-3.93 (m, 2H), 4.94-4.98 (m, 1H), 7.11 (t, 1H), 7.37 (m, 2H), 7.61-7.67 (m, 2H), 8.00 (d, 1H), 9.11 (s, 1H). MS (+ESI) m/z 397 (MH+).

Aufarbeitung

  1. temperaturethe mixture was heated at 65-70° C. for 6 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed twice with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3eec4911fb6d40568dbefcf2df079463
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799787B2

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