Triethylamine → HCID 59836010, Verbindung

HRID 272019

Reaktionsgleichung

Reaktionsgleichung von HRID 272019
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=3)[C:14]([OH:16])=O)[CH:9]=2)[N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:3]=1.[CH3:28][N:29]([CH3:38])[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:28][N:29]([CH3:38])[CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][N:35]([C:14]([C:13]2[CH:17]=[CH:18][CH:19]=[C:11]([C:8]3[CH:9]=[C:10]4[C:2]([I:1])=[N:3][N:4]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:25])[CH3:26])[C:5]4=[N:6][CH:7]=3)[CH:12]=2)=[O:16])[CH2:34][CH2:33]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 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 59836117HCID 59836117, Verbindung

Produkt 1

HCID 59836010HCID 59836010, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of crude 3-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)benzoic acid (200 mg, 0.404 mmol), N,N-dimethyl-2-(piperazin-1-yl)ethanamine (76 mg, 0.485 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (185 mg, 0.485 mmol), triethyl amine (0.700 ml, 0.485 mmol) and in DMF (2 ml) was stirred at 90° C. in Personal Microwave for 1 hour. Water was then added to the mixture and extracted with ethyl acetate (3×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to dryness. Silica gel chromatography of the crude product afforded (4-(2-(dimethylamino)ethyl)piperazin-1-yl)(3-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)methanone (110 mg, 43% yield) as off-white solids. MS: m/z 635.1 (M+H+).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a84bc1bc74e2486c81facd6c4f1da4ec
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452993B2

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