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1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamide

HRID 930329
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Reaktionsgleichung

Reaktionsgleichung von HRID 930329
C([NH:9][C:10]1[O:11][C@H:12]([C:35]([F:38])([F:37])[F:36])[CH2:13][C@:14]([C:17]2[CH:18]=[C:19]([NH:24][C:25]([N:27]3[CH2:32][CH2:31][CH:30]([O:33][CH3:34])[CH2:29][CH2:28]3)=[O:26])[CH:20]=[CH:21][C:22]=2[F:23])([CH3:16])[N:15]=1)(=O)C1C=CC=CC=1.N12CCCN=C1CCCCC2>CO>[NH2:9][C:10]1[O:11][C@H:12]([C:35]([F:36])([F:38])[F:37])[CH2:13][C@:14]([C:17]2[CH:18]=[C:19]([NH:24][C:25]([N:27]3[CH2:28][CH2:29][CH:30]([O:33][CH3:34])[CH2:31][CH2:32]3)=[O:26])[CH:20]=[CH:21][C:22]=2[F:23])([CH3:16])[N:15]=1
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Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86732157N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamide

Produkt 1

HCID 86732158N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of N-(3-((4S,6S)-2-benzamido-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-4-methoxypiperidine-1-carboxamide (0.166 g, 0.309 mmol) in MeOH (3 mL) at room temperature was added 1,8-diazabicyclo-[5.4.0]undec-7-ene (0.100 mL, 0.669 mmol). The reaction was heated at 60° C. for 4 h. Then the reaction was cooled to room temperature, diluted with MeOH, purified by reverse-phase HPLC (Gilson; Gemini-NX 10m C18 110A AXIA, 100×50 mm column) eluting with 0.1% TFA-H2O:0.1% TFA CH3CN (9:1→1:9). The fractions containing the desired product were combined and concentrated in vacuo. The material was dissolved in MeOH and eluted with MeOH, through an Silicycle carbonate cartridge to give the titled compound as a white crystalline solid (68 mg, 51%). MS m/z=433 [M+H]+. Calculated for C19H24F4N4O3: 432

Aufarbeitung

  1. temperatureThen the reaction was cooled to room temperature
  2. custompurified by reverse-phase HPLC (Gilson
  3. washGemini-NX 10m C18 110A AXIA, 100×50 mm column) eluting with 0.1% TFA-H2O
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated in vacuo
  6. dissolutionThe material was dissolved in MeOH
  7. washeluted with MeOH, through an Silicycle carbonate cartridge

Quellen und Nachweise

ORD-Eintrag
ord-da3b2fa1ef8b4e448ba0f07293efdf10
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296734B2

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