Sodium Hydroxide → 2-(3,5-Diphenyl-pyrazol-1-yl)-1-(4-(2-pyrimidinyl)-1-piperazinyl)-ethanon

HRID 68563

Reaktionsgleichung

Reaktionsgleichung von HRID 68563
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19](O)=[O:20])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[N:53]1([C:59]2[N:64]=[CH:63][CH:62]=[CH:61][N:60]=2)[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.[OH-].[Na+]>CN(C=O)C.C(Cl)Cl>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:9]([CH2:18][C:19]([N:56]3[CH2:57][CH2:58][N:53]([C:59]4[N:60]=[CH:61][CH:62]=[CH:63][N:64]=4)[CH2:54][CH2:55]3)=[O:20])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

8

Edukt 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 824607(3,5-Diphenyl-pyrazol-1-yl)-acetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 867626722-(3,5-Diphenyl-pyrazol-1-yl)-1-(4-(2-pyrimidinyl)-1-piperazinyl)-ethanonAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

278 mg (3,5-diphenyl-pyrazol-1-yl)-acetic acid was dissolved in 5 mL DMF. 321 mg TBTU and 172 μL DIPEA were added to this solution and the mixture was stirred for a few minutes at RT. 164 mg 2-(1-piperazinyl)-pyrimidine was added and stiffing was continued for 30 min. Then 10 mL of a 1M NaOH solution and 50 mL CH2Cl2 were added, the organic phase was separated. The solvent was removed and the residue was purified by flash chromatography (silica gel, DCM/MeOH/NH3 0-5%). Diethylether was given to the residue and the precipitate was filtered to yield 310 mg of the desired compound.

Aufarbeitung

  1. customthe organic phase was separated
  2. customThe solvent was removed
  3. customthe residue was purified by flash chromatography (silica gel, DCM/MeOH/NH3 0-5%)
  4. filtrationthe precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-49b5a83dc13b4d57b96ba0b47e36f155
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822464B2

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