Water → Convergence

HRID 418294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418294
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N:20]1[N:24]2[CH:25]=[CH:26][CH:27]=[N:28][C:23]2=[C:22]([C:29](O)=[O:30])[CH:21]=1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:19][C:2]([F:1])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:29]([C:22]3[CH:21]=[N:20][N:24]4[CH:25]=[CH:26][CH:27]=[N:28][C:23]=34)=[O:30])[CH2:14][CH2:13]2)(=[O:10])=[O:11])=[CH:7][CH:8]=1

Komponenten

8

Edukt 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 25545781-[4-(Trifluoromethyl)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 59152103ConvergenceAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Description 1) (200 mg, 0.680 mmol) in DMF (5 ml) was added pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (111 mg, 0.680 mmol), HOBT.H2O (104 mg, 0.680 mmol) and HBTU (258 mg, 0.680 mmol). Finally DIPEA (0.356 ml, 2.039 mmol) was added and the reaction mixture was stirred at rt for 20 hours. Solvent was removed by evaporation, the crude partitioned between DCM (50 ml) and saturated aq. sodium bicarbonate (50 ml), the DCM layer collected, dried (hydrophobic frit) and evaporated. MDAP purification yielded the title compound (317 mg) as an off-white solid.

Aufarbeitung

  1. customSolvent was removed by evaporation
  2. customthe crude partitioned between DCM (50 ml) and saturated aq. sodium bicarbonate (50 ml)
  3. customthe DCM layer collected
  4. customdried (hydrophobic frit)
  5. customevaporated
  6. customMDAP purification

Quellen und Nachweise

ORD-Eintrag
ord-48aa982af32e44d6ad25a834957fe306
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093249B2

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