Sodium Carbonate → HCID 178489389, Verbindung

HRID 272027

Reaktionsgleichung

Reaktionsgleichung von HRID 272027
[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]([OH:23])=O)[CH:16]=2)[NH:11][N:10]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:51][N:52]([CH3:61])[CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CO.ClCCl>[CH3:51][N:52]([CH3:61])[CH2:53][CH2:54][N:55]1[CH2:60][CH2:59][N:58]([C:21]([C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([C:15]3[CH:16]=[C:17]4[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])=[N:10][NH:11][C:12]4=[N:13][CH:14]=3)[CH:19]=2)=[O:23])[CH2:57][CH2:56]1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 27362291-(2-(Dimethylamino)ethyl)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 178489389HCID 178489389, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid (338 mg, 0.79 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (300 mg, 0.79 mmol) were dissolved in a mixture of 20 ml of acetonitrile and 10 ml of methanol. 131 mg (0.83 mmol) of 1-(2-dimethylaminoethyl)-piperazine was added and the mixture stirred at ambient temperature for 6 h. The resulting mixture was distributed between dichloromethane and a 2 M aqueous solution of sodium carbonate. The phases were separated and the aqueous layer extracted three times with dichloromethane. The combined organic layers were combined, washed with a saturated aqueous solution of sodium bromide, dried over sodium sulfate, and evaporated. The crude material was purified by flash chromatography on silica gel using a stepped gradient of ethyl acetate and a 4:4:1 solvent mixture of ethyl acetate, dichloromethane and methanol containing 2% v/v of 35% wt ammonia in water to afford [4-(2-dimethylamino-ethyl)-piperazin-1-yl]-{3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-methanone (160 mg, 42%) as an oil. 1H-NMR (d6-CDCl3) δ: 8.87 (d) [1H], 8.36 (d) [1H], 7.75 (dd) [1H], 7.68 (t) [1H], 7.67 (m) [1H], 7.53 (m) [1H], 7.46 (mt) [1H], 7.42 (md) [1H], 7.13 (dt) [1H], 7.10 (d) [1H], 3.89 (s) [3H], 3.81-3.86 (m) [2H], 3.48-3.55 (m) [2H], 2.58-2.64 (m) [2H], 2.56 (m) [2H], 2.50 (m) [2H], 2.44-2.52 (m) [2H]. MS: m/z 485 (M+H+).

Aufarbeitung

  1. customThe phases were separated
  2. extractionthe aqueous layer extracted three times with dichloromethane
  3. washwashed with a saturated aqueous solution of sodium bromide
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude material was purified by flash chromatography on silica gel using a stepped gradient of ethyl acetate
  7. additiona 4:4:1 solvent mixture of ethyl acetate, dichloromethane and methanol containing 2% v/v of 35% wt ammonia in water

Quellen und Nachweise

ORD-Eintrag
ord-20e05f11f36a400682b704a5faa94fe5
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452993B2

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