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Diisopropylethylamine → (2-{1-[2,6-Bis-(4-cyano-phenoxy)-pyridine-3-carbonyl]-piperidin-4-yl}-ethyl)-carbamic Acid Tert-butyl Ester

HRID 1024681
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1024681
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[N:16]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH:14]=[CH:13][C:9]=2[C:10](O)=[O:11])=[CH:5][CH:4]=1)#[N:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[C:70]([O:74][C:75](=[O:85])[NH:76][CH2:77][CH2:78][CH:79]1[CH2:84][CH2:83][NH:82][CH2:81][CH2:80]1)([CH3:73])([CH3:72])[CH3:71]>CN(C=O)C>[C:70]([O:74][C:75](=[O:85])[NH:76][CH2:77][CH2:78][CH:79]1[CH2:80][CH2:81][N:82]([C:10]([C:9]2[C:8]([O:7][C:6]3[CH:26]=[CH:27][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)=[N:16][C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)=[O:11])[CH2:83][CH2:84]1)([CH3:73])([CH3:71])[CH3:72]
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Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 15018494-(2-Aminoethyl)piperidine, 4-BOC protectedHCID 2724699PyBOPHCID 676059982,6-Bis(4-cyanophenoxy)-nicotinic acid

Produkt 1

HCID 66818540(2-{1-[2,6-Bis-(4-cyano-phenoxy)-pyridine-3-carbonyl]-piperidin-4-yl}-ethyl)-carbamic Acid Tert-butyl Ester

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 2,6-Bis-(4-cyano phenoxy)-nicotinic acid, 0.335 g (0.94 mmol), in 5 ml of DMF was added dropwise to the stirred suspension of 0.489 g (0.94 mmol) of benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBop) in 5 ml of DMF and followed by N,N-diisopropylethylamine 0.242 g (1.88 mmol) while the temperature was maintained below 5° C. during the addition. The mixture was stirred for 10 min and a solution of (2-piperidin-4-yl-ethyl)-carbamic acid tert-butyl ester (0.214 g, 0.94 mmol) in 2 ml of DMF was added. The mixture was stirred overnight at RT. The solvent was concentrated under reduced pressure and the residue was dissolved in a mixture of water (150 ml) and ethyl acetate (150 ml). The pH was adjusted to 2-3 with 6 N HCl and the phases were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with 10% solution of potassium hydrogen sulphate followed by saturated sodium bicarbonate solutiona and saturated brine solution, and dried over sodium sulphate and concentrated. The crude oily residue was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 0.4 g of the required product. Percentage purity: 36.3%, (M+1)=567.2. 1H NMR (DMSO-d6): δ 1.35 (3H, m), 1.38 (9H, s), 1.65 (2H, m), 2.71 (2H, m), 2.95 (4H, m), 3.75 (2H, m), 6.80 (1H, t), 6.95 (1H, d), 7.32 (4H, d), 7.68 (1H, m), 7.85 (4H, d).

Aufarbeitung

  1. temperaturewas maintained below 5° C. during the addition
  2. stirringThe mixture was stirred overnight at RT
  3. concentrationThe solvent was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in a mixture of water (150 ml) and ethyl acetate (150 ml)
  5. customthe phases were separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washThe combined organic phase was washed with 10% solution of potassium hydrogen sulphate
  8. dry with materialand saturated brine solution, and dried over sodium sulphate
  9. concentrationconcentrated
  10. customThe crude oily residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eaab48293a2748bdbd0b4271ee4fdea5
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08722930B2

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