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Potassium Carbonate → Ammonia

HRID 1276150
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1276150
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[C:22]([NH:24][CH2:25][CH2:26][N:27]1[C@H:32]([CH3:33])[CH2:31][NH:30][CH2:29][C@@H:28]1[CH3:34])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH3:4].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[C:22]([NH:24][CH2:25][CH2:26][N:27]1[C@@H:32]([CH3:33])[CH2:31][N:30]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:29][C@H:28]1[CH3:34])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 61277Isopropyl isocyanateHCID 9821522(2S)-1-(1,3-benzoxazol-2-yl)-N2-2-[(cis)-2,6-dimethyl-1-piperazinyl]ethyl-2-piperidinecarboxamide

Produkt 2

HCID 222AmmoniaHCID 9869349(cis)-4-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]-N1-isopropyl-3,5-dimethyl-1-piperazinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Isopropylisocyanate (0.029 ml) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2 -2-[(cis)-2,6-dimethyl-1-piperazinyl]ethyl-2-piperidinecarboxamide (105 mg) [see Example 8] and potassium carbonate (37.5 mg) in acetonitrile (3. ml). The reaction mixture was stirred at room temperature for 5 hours, after which time the solvent was removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 94.6:5.6:0.8 changing to 93:7; 1, by volume, dichloromethane: methanol: 0.88 aqueous ammonia solution to afford (cis)-4-[2-([(2S)-1-(1,3-benzoxazol-2-yl)-2-piperidinyl]carbonylamino)ethyl]-N1 -isopropyl-3,5-dimethyl-1-piperazinecarboxamide (72.8 mg) as a white solid.

Aufarbeitung

  1. customafter which time the solvent was removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 94.6:5.6:0.8 changing to 93:7

Quellen und Nachweise

ORD-Eintrag
ord-460c2754162442b486342e9e5700a7a7
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06166011

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