1-(2-Pyrimidinyl)piperazine → HCID 178489387, Verbindung

HRID 272040

Reaktionsgleichung

Reaktionsgleichung von HRID 272040
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])[CH:16]=2)[NH:11][N:10]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:51]1[CH:56]=[CH:55][CH:54]=[N:53][C:52]=1[N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([C:21]([N:60]4[CH2:61][CH2:62][N:57]([C:52]5[N:51]=[CH:56][CH:55]=[CH:54][N:53]=5)[CH2:58][CH2:59]4)=[O:22])[CH:24]=[CH:25][CH:26]=3)[CH:16]=2)[NH:11][N:10]=1

Komponenten

5

Edukt 3

HCID 887471-(2-Pyrimidinyl)piperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178489390HCID 178489390, Verbindung

Produkt 1

HCID 178489387HCID 178489387, VerbindungAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid (18 mg, 0.05 mmol) in DMF (1 mL) was added HATU (20 mg, 0.05 mmol) and 1-(2-pyrimidyl)piperazine (11 uL, 0.08 mmol). The reaction solution was stirred for 16 hours at ambient temperature. The crude product was extracted into ethyl acetate and washed with H2O. The organic layer was dried over Na2SO4, filtered, and adsorbed onto silica gel. Purification by flash chromatography with a gradient of ethyl acetate (containing 10% MeOH) and hexanes afforded the title compound as a white powder (7.2 mg, 28% yield). 1H NMR (500 MHz, CD3OD) δ 8.85 (d, J=2 Hz, 1H), 8.42 (d, J=2 Hz, 1H), 8.35 (d, J=4.5 Hz, 2H), 7.83 (d, J=8 Hz, 1H), 7.79 (s, 1H), 7.64 (m, 2H), 7.50 (m, 2H), 7.20 (d, J=8.5 Hz, 1H), 7.11 (t, J=8 Hz, 1H), 6.64 (t, J=4.5 Hz, 1H), 3.96 (br s, 2H), 3.89 (s, 3H), 3.86 (br s, 4H), 3.60 (br s, 2H). MS: m/z 492.1 (M+H+).

Aufarbeitung

  1. extractionThe crude product was extracted into ethyl acetate
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customPurification by flash chromatography with a gradient of ethyl acetate (containing 10% MeOH) and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c69ad9bfa3ab4dbc8a5da77444f6fe63
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452993B2

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