Trifluoroacetic acid → HCID 178485287, Verbindung

HRID 238539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238539
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]#[N:17])[CH2:12][CH2:11]1)[C:3](=[O:9])OC(C)(C)C.FC(F)(F)C(O)=O.[N:25]1[O:26][N:27]=[C:28]2[CH:33]=[C:32](C(Cl)=O)[CH:31]=[CH:30][C:29]=12>ClCCl>[C:16]([C@@H:13]1[CH2:12][CH2:11][C@H:10]([N:2]([CH3:1])[C:3]([C:32]2[CH:31]=[CH:30][C:29]3=[N:25][O:26][N:27]=[C:28]3[CH:33]=2)=[O:9])[CH2:15][CH2:14]1)#[N:17]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 27354532,1,3-Benzoxadiazole-5-carbonyl chlorideHCID 66725780t-Butyl methyl-(4-cyanocyclohexyl)carbamate

Produkt 1

HCID 178485287HCID 178485287, VerbindungAusbeute 19,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

t-Butyl methyl-(4-cyanocyclohexyl)carbamate (710 mg, 3 mmol) was dissolved in dichloromethane (20 ml) and trifluoroacetic acid (3 ml) was added. The solvent was evaporated after 2 hours, the residue was re-dissolved in a 4N HCl (3 ml) solution in dioxane and the solvent evaporated. Dichloromethane (30 ml) and NEt3 (2 ml) were added to the residue followed by a solution of [2,1,3]-benzoxadiazole-5-carbonylchloride (548 mg, 3 mmol) in dichloromethane (10 ml). After stirring the mixture for 1 hour at room temperature, the organic phase was washed with 1N HCl and conc. NaHCO3 solution, dried over magnesium sulfate, and concentrated under vacuum. The material was purified on a silica gel column eluting with ethyl acetate/chloroform (1:1) to give 170 mg of N-(cis-4-cyanocyclohexyl)-N-methyl-[2,1,3]-benzoxadiazole-5-carboxamide as a white solid and as the less polar isomer. Mp=222-223° C., 1H NMR (300 MHz, CDCl3, rotamers) δ 7.93 (d, 1H, J=9.0 Hz); 7.85 (s, 1H), 7.42 (d, J=9.0 Hz, 1H); 4.65-4.50 and 3.55-3.40 and 3.15-2.80 (m, 5H) and 2.20-1.30 ppm (m, 8H).

Aufarbeitung

  1. customThe solvent was evaporated after 2 hours
  2. dissolutionthe residue was re-dissolved in a 4N HCl (3 ml) solution in dioxane
  3. customthe solvent evaporated
  4. additionDichloromethane (30 ml) and NEt3 (2 ml) were added to the residue
  5. washthe organic phase was washed with 1N HCl and conc. NaHCO3 solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe material was purified on a silica gel column
  9. washeluting with ethyl acetate/chloroform (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8c7bfc92fbe845c3b0eefadde54e9727
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642633B2

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