Diisopropylethylamine → (R)-4-[6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-(2,2,2-trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 2279159Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279159
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([C:27](O)=[O:28])[C:14]3[C:19]([CH3:20])=[N:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:15]=3[N:16]=2)=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][NH:49][C@H:48]([CH2:52][C:53]([F:56])([F:55])[F:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:41])[CH3:40]>C(Cl)Cl.O>[C:39]([O:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:27]([C:13]2[C:14]3[C:19]([CH3:20])=[N:18][N:17]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:15]=3[N:16]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:6][CH:7]=3)[CH:12]=2)=[O:28])[C@H:48]([CH2:52][C:53]([F:55])([F:56])[F:54])[CH2:47]1)=[O:45])([CH3:42])([CH3:40])[CH3:41]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 72210106(R)-3-(2,2,2-Trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl esterHCID 900138076-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Produkt 1

HCID 90013556(R)-4-[6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-3-(2,2,2-trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl esterAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 0.80 g of 6-(4-methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid in 12 ml of DCM were added 1 ml of Hünig's base, 0.48 g of BEP and 0.50 g of (R)-3-(2,2,2-trifluoroethyl)-piperazine-1-carboxylic acid tert-butyl ester. The reaction was stirred at r.t. for 2 d. For workup it was diluted with water and DCM and the layers were separated. The organic layer was washed with water twice, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/EtOAc gradient) to obtain 0.58 g (60%) of the title compound.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (silica, heptane/EtOAc gradient)

Quellen und Nachweise

ORD-Eintrag
ord-88ee32782b944209b60c3720f6321a5d
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133181B2

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