Piperidine → HCID 11705955, Verbindung

HRID 20569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20569
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[C:25]([C:27]([NH:29][C:30]2[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=2)=[O:28])[CH:24]=[C:23]([O:36][C@@H:37]([CH3:40])[CH2:38][OH:39])[CH:22]=1)[C:14]([OH:16])=O.CN(C(ON1N=N[C:51]2[CH:52]=[CH:53][CH:54]=[N:55][C:50]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C.O>[F:10][C:11]1[CH:12]=[C:13]([C:14]([N:55]2[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]2)=[O:16])[CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[C:25]([CH:24]=[C:23]([O:36][C@@H:37]([CH3:40])[CH2:38][OH:39])[CH:22]=1)[C:27]([NH:29][C:30]1[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=1)=[O:28]

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593469353-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

Produkt 1

HCID 11705955HCID 11705955, VerbindungAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (0.36 mL, 1.95 mmol) was added to a suspension of 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid (209 mg, 0.49 mmol), HATU (390 mg, 1.02 mmol) and piperidine (0.19 mL, 1.95 mmol) in DMF (3 mL), and the mixture stirred at ambient temperature for 24 hours. Water (30 mL) was added and the mixture extracted with diethyl ether/ethyl acetate 4:1 (3×20 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-20% methanol in ethyl acetate, to give the desired compound (116 mg).

Aufarbeitung

  1. extractionthe mixture extracted with diethyl ether/ethyl acetate 4:1 (3×20 mL)
  2. washThe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue which
  5. customwas chromatographed on silica
  6. washeluting with a gradient of 0-20% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d5344cbb75354419b82a61858da94bef
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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