1,2-Dichloroethane → Tert-butyl 4-(2-{(cyclohexylcarbonyl) [(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

HRID 1943027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943027
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][NH:13][CH2:14][CH:15]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]1=[O:35].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH:59]1([C:65](O)=[O:66])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1>C(Cl)Cl>[CH:59]1([C:65]([N:13]([CH2:12][C:4]2[C:3](=[O:35])[N:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:14][CH:15]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:24][CH2:23]2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:66])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 58415941Tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

Produkt 1

HCID 58415912Tert-butyl 4-(2-{(cyclohexylcarbonyl) [(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate (1.61 g crude, 3.39 mmol), EDC (1.298 g, 6.77 mmol), HOAT (0.461 g, 3.39 mmol), DIEA (1.182 ml, 6.77 mmol), and cyclohexanecarboxylic acid (0.504 ml, 4.06 mmol) were combined in CH2Cl2 and the reaction stirred for 15 hours. The mixture was partitioned between CH2Cl2 and satd. bicarb, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was purified by silica gel chromatography on an Isco Companion. The desired fractions were combined and concentrated in vacuo. 1.63 g, 82% over two steps.

Aufarbeitung

  1. customThe mixture was partitioned between CH2Cl2 and satd
  2. extractionbicarb, the aqueous portion extracted 3×CH2Cl2
  3. dry with materialthe organic portion dried (Na2SO4)
  4. concentrationthen concentrated in vacuo
  5. customThe resulting material was purified by silica gel chromatography on an Isco Companion
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dd00ba19f87b40e5b7bac85a36329e7d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389720B2

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