tert-butyl N-(prop-2-yn-1-yl)carbamate → tert-Butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamate

HRID 1247591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247591
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](I)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:24]#[CH:25]>C(#N)C.C(N(CC)CC)C>[C:1]12([CH2:11][NH:12][C:13]([C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:25]#[C:24][CH2:23][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH:15]=3)=[O:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

5

Edukt 2

HCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamateHCID 21906675N-(1-adamantylmethyl)-5-chloro-2-iodoisonicotinamide

Produkt 1

HCID 21906674tert-Butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamateAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A suspension of N-(1-adamantylmethyl)-5-chloro-2-iodoisonicotinamide (Example2(i)) (0.43 g) and tert-butyl prop-2-ynylcarbamate, (0.31 g) in anhydrous acetonitrile (5 ml) and triethylamine (5 ml) was purged with nitrogen for 5 minutes and the copper (I) iodide (0.004 g) and bis-triphenyphosphine palladium dichloride (0.014 g) were added. The mixture was stirred under nitrogen for 0.75 hours. The mixture was concentrated and the residue was purified by chromatography on silica gel eluting with acetone:dichloromethane (1:19) to afford the sub-titled compound (0.34 g) as a yellow foam.

Aufarbeitung

  1. customwas purged with nitrogen for 5 minutes
  2. additionthe copper (I) iodide (0.004 g) and bis-triphenyphosphine palladium dichloride (0.014 g) were added
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by chromatography on silica gel eluting with acetone:dichloromethane (1:19)

Quellen und Nachweise

ORD-Eintrag
ord-8bab744f2d184a70b0f0f08a29c1889c
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129246B2

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