Diisopropylethylamine → 1-tert-Butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(1,3-oxazol-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl) (2-methylpropyl)amino]piperidine-1,3-dicarboxylate

HRID 2192796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192796
[C:1]([C:5]1[N:10]=[C:9](Cl)[C:8]([C:12]([N:14]([CH2:32][CH:33]([CH3:35])[CH3:34])[C@@H:15]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][C@H:17]([C:28]([O:30][CH3:31])=[O:29])[CH2:16]2)=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl.[O:46]1[CH:50]=[CH:49][N:48]=[C:47]1[CH2:51][NH2:52]>CC(O)C>[C:1]([C:5]1[N:10]=[C:9]([NH:52][CH2:51][C:47]2[O:46][CH:50]=[CH:49][N:48]=2)[C:8]([C:12]([N:14]([CH2:32][CH:33]([CH3:35])[CH3:34])[C@@H:15]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][C@H:17]([C:28]([O:30][CH3:31])=[O:29])[CH2:16]2)=[O:13])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 469120601-(1,3-Oxazol-2-yl)methanamine hydrochlorideHCID 593565701-tert-butyl 3-methyl (3R*,5S*)-5-{[(2-tert-butyl-4-chloropyrimidin-5-yl)carbonyl](isobutyl)amino}piperidine-1,3-dicarboxylate

Produkt 1

HCID 596253251-tert-Butyl 3-methyl (3R,5S)-5-[({2-tert-butyl-4-[(1,3-oxazol-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl) (2-methylpropyl)amino]piperidine-1,3-dicarboxylateAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-tert-butyl 3-methyl (3R,5S)-5-{[(2-tert-butyl-4-chloropyrimidin-5-yl)carbonyl](isobutyl)amino}piperidine-1,3-dicarboxylate (0.55 g) and diisopropylethylamine (0.87 ml) in 2-propanol (5 ml) was added 2-oxazolylmethylamine hydrochloride (0.34 g), and the mixture was stirred at 80° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and the fraction eluted with hexane to ethyl acetate-hexane (1:2) was concentrated under reduced pressure to give the object compound (525 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washthe fraction eluted with hexane to ethyl acetate-hexane (1:2)
  7. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9b3b2a7df4b448a29d801ea25a566e67
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329691B2

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