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Water → 5-Methyl-N-{3-methyl-[1-(oxetan-3-yl)piperidin-4-yl]pyridin-5-yl}-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide

HRID 1748662
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1748662
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:20][C:21]1[N:25]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][N:27]=2)[N:24]=[CH:23][C:22]=1[C:36]([NH:38][C:39]1[CH:40]=[N:41][C:42]([CH:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)=[C:43]([CH3:45])[CH:44]=1)=[O:37].O>ClCCl>[CH3:20][C:21]1[N:25]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:28][N:27]=2)[N:24]=[CH:23][C:22]=1[C:36]([NH:38][C:39]1[CH:44]=[C:43]([CH3:45])[C:42]([CH:46]2[CH2:51][CH2:50][N:49]([CH:3]3[CH2:2][O:1][CH2:4]3)[CH2:48][CH2:47]2)=[N:41][CH:40]=1)=[O:37]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 866925445-Methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide

Produkt 1

HCID 866926035-Methyl-N-{3-methyl-[1-(oxetan-3-yl)piperidin-4-yl]pyridin-5-yl}-1-[5-(trifluoromethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxamide
Ausbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Oxetanone (121 mg) and sodium triacetoxyborohydride (143 mg) were added at room temperature to a solution of 5-methyl-N-[5-methyl-6-(piperidin-4-yl)pyridin-3-yl]-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (250 mg) described in Reference Example 171 in dichloromethane (24 ml), and stirred at the same temperature for five hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic solution was dried over anhydrous sodium sulfate and concentrated. 1N Aqueous solution of sodium hydroxide (20 ml) was added to the resulting residue, solid was collected by filtration purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (100 mg) as a white solid.

Aufarbeitung

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. addition1N Aqueous solution of sodium hydroxide (20 ml) was added to the resulting residue, solid
  6. filtrationwas collected by filtration
  7. custompurified with silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-1350512077bb4267a3eeef7377b42839
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150555B2

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