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Water → N-((1-(4-Methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-methoxyphenylamino) nicotinamide

HRID 626381
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 626381
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:21]=[CH:20][CH:19]=[CH:18][C:11]=2[C:12]([NH:14][CH2:15][C:16]#[CH:17])=[O:13])=[CH:5][CH:4]=1.[N:22]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](OC2C=CC=CC=2)[CH:27]=1)=[N+:23]=[N-:24].O.[O:40]=[C:41]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>S([O-])([O-])(=O)=O.[Cu+2].C(O)(C)(C)C>[CH3:41][O:40][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:22]2[CH:17]=[C:16]([CH2:15][NH:14][C:12](=[O:13])[C:11]3[CH:18]=[CH:19][CH:20]=[N:21][C:10]=3[NH:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[N:24]=[N:23]2)=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 23667548Sodium AscorbateHCID 581200811-(Azidomethyl)-3-phenoxybenzeneHCID 1181259512-(4-methoxyphenylamino)-N-(prop-2-ynyl)nicotinamide

Produkt 1

HCID 90681011N-((1-(4-Methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-methoxyphenylamino) nicotinamideAusbeute 708,7 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 24462Copper SulfateKatalysatorHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Compound 8 (194 mg, 1 mmol) and 4-methoxyaniline (9e, 123 mg, 1 mmol) were taken in ethylene glycol and heated at 140° C. for 6 h. Then the reaction mixture was cooled and extracted with ethyl acetate from the aqueous layer and concentrated in vacuum. The compound was further purified by column chromatography using 60-120 silica gel to obtain 2-(4-methoxyphenylamino)-N-(prop-2-ynyl)nicotinamide 10e as pure product. To a solution of 2-(4-methoxyphenylamino)-N-(prop-2-ynyl)nicotinamide (10e, 150 mg, 0.53 mmol) and 1-(azidomethyl)-4-methoxybenzene (12c, 95 mg, 0.58 mmol) in 2:1 mixture of water and tert-butyl alcohol, sodium ascorbate (0.06 mmol) and copper (II) sulphate (0.005 mmol) were added sequentially. The reaction was stirred at room temperature for 12 h, TLC analysis indicated completion of reaction. The reaction mixture was concentrated under vacuum and extracted with EtOAc to give crude product. The crude was purified by column chromatography to afford pure product 5e (189 mg, 80%); %); 1H NMR (300 MHz, CDCl3) δ 10.31 (s, 1H), 8.19 (dd, J=4.9, 1.7 Hz, 1H), 7.7.81 (dd, J=7.7, 1.7 Hz, 2H), 7.52-7.48 (m, 3H), 7.25-7.19 (m, 2H), 6.85-6.81 (m, 4H), 6.55-6.51 (m, 1H), 5.42 (s, 2H), 4.55 (d, J=5.4 Hz, 2H), 3.78 (s, 3H), 3.77 ppm (s, 3H); yield 80%

Aufarbeitung

  1. additionwere added sequentially
  2. customcompletion of reaction
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. extractionextracted with EtOAc
  5. customto give crude product
  6. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0ca259572957427f994960e34f4b279b
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309225B2

Notizen zur Reaktion

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