Trifluoroacetic acid → 1-{2-[6-(3,3-Difluoropyrrolidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

HRID 2039499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039499
Cl[C:2]1[CH:7]=[C:6]([NH:8][NH2:9])[N:5]=[CH:4][N:3]=1.Cl.[F:11][C:12]1([F:17])[CH2:16][CH2:15][NH:14][CH2:13]1.C(N(C(C)C)C(C)C)C.FC(F)(F)C(O)=O.CN(C)[CH:36]=[C:37]([N:43]1[CH:47]=[C:46]([C:48]#[N:49])[N:45]=[N:44]1)[C:38](OCC)=[O:39]>O>[F:11][C:12]1([F:17])[CH2:16][CH2:15][N:14]([C:2]2[N:3]=[CH:4][N:5]=[C:6]([N:8]3[C:38](=[O:39])[C:37]([N:43]4[CH:47]=[C:46]([C:48]#[N:49])[N:45]=[N:44]4)=[CH:36][NH:9]3)[CH:7]=2)[CH2:13]1

Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 2472224-Chloro-6-hydrazinylpyrimidineHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 66725972Ethyl 2-(4-cyanotriazol-1-yl)-3-(dimethylamino)prop-2-enoate

Produkt 1

HCID 444648701-{2-[6-(3,3-Difluoropyrrolidin-1-yl)pyrimidin-4-yl]-3-oxo-2,3-dihydro-1H-pyrazol-4-yl}-1H-1,2,3-triazole-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 200 mg (1.4 mmol) of the compound from Example 11A, 238 mg (1.7 mmol) of 3,3-difluoropyrrolidine hydrochloride and 289 μl (215 mg, 1.7 mmol) of N-ethyl-N-(propan-2-yl)propane-2-amine in 3 ml of water is stirred at 100° C. for 16 h. Following the addition of 53 μl (79 mg, 0.7 mmol) of trifluoroacetic acid and 325 mg (1.4 mmol) of the compound from Example 7A, the reaction mixture is stirred at 100° C. for 16 h. The precipitated solid is filtered off and washed first with water and then with diethyl ether. The product is dried under reduced pressure. Yield: 137 mg (27% of theory)

Aufarbeitung

  1. stirringthe reaction mixture is stirred at 100° C. for 16 h
  2. filtrationThe precipitated solid is filtered off
  3. washwashed first with water
  4. customThe product is dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35473aa18f8b40dc98ffe74910fd584a
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580778B2

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