Trifluoroacetic acid → 2-((R)-1-(2,4-dichlorophenyl)ethylamino)-4-(4-((R)-piperidine-2-carbonyl)piperazin-1-yl)benzonitrile

HRID 75138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 75138
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][N:25]3C(OC(C)(C)C)=O)=[O:23])[CH2:18][CH2:17]2)=[CH:12][C:11]=1[NH:37][C@@H:38]([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=1[Cl:47])[CH3:39])#[N:9]>ClCCl>[Cl:47][C:41]1[CH:42]=[C:43]([Cl:46])[CH:44]=[CH:45][C:40]=1[C@H:38]([NH:37][C:11]1[CH:12]=[C:13]([N:16]2[CH2:17][CH2:18][N:19]([C:22]([C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]3)=[O:23])[CH2:20][CH2:21]2)[CH:14]=[CH:15][C:10]=1[C:8]#[N:9])[CH3:39]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86689056(R)-t-butyl 2-(4-(4-cyano-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperazine-1-carbonyl)piperidine-1-carboxylate

Produkt 1

HCID 715819522-((R)-1-(2,4-dichlorophenyl)ethylamino)-4-(4-((R)-piperidine-2-carbonyl)piperazin-1-yl)benzonitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.3 mL) was added to a solution of (R)-t-butyl 2-(4-(4-cyano-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperazine-1-carbonyl)piperidine-1-carboxylate (0.095 g, 0.16 mmol) in dichloromethane (1 mL) at room temperature, and the solution was stirred for 1 h. Excess solvent was removed in vacuo, and the residue was diluted with dichloromethane. The organic layer was neutralized with aqueous saturated sodium bicarbonate solution, and the aqueous layer was further extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound as a white solid (0.060 g, 0.12 mmol, 75%). 1H NMR (400 MHz, DMSO-d6) δ 9.0 (br, 1H), 8.62-8.52 (m, 1H), 7.62-7.50 (m, 2H), 7.37 (dd, J=2.2, 8.4 Hz, 1H), 7.05 (d, J=8.8 Hz, 1H), 6.19 (dd, J=2.5, 8.8 Hz, 1H), 5.82 (d, J=2.6 Hz, 1H), 5.68 (br, 1H), 4.86 (br, 1H), 3.70-2.80 (m, 9H), 1.98-1.92 (m, 1H), 1.78-1.58 (m, 4H), 1.50-1.40 (m, 5H); MS: (ES) m/z calculated for C25H30Cl2N5O [M+H]+ 486.2. found 486.

Aufarbeitung

  1. customExcess solvent was removed in vacuo
  2. additionthe residue was diluted with dichloromethane
  3. extractionthe aqueous layer was further extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ed99b1872fc04839acc6446d708eea5d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835419B2

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