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Triphenylphosphine → 3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 62449
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 62449
[S:1]([N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH:15](O)[C:14]=2[CH:13]=[N:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])[NH:24][N:23]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])[N:24]([CH:15]2[CH2:16][CH2:17][CH2:18][C:19]3[N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:2])=[O:3])[N:12]=[CH:13][C:14]2=3)[N:23]=1
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Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 903041681-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-olHCID 178491029HCID 178491029, Verbindung

Produkt 1

HCID 903039373-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
Ausbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (4.05 g, 11.13 mmol), 3-bromo-N-(2,4-dimethoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3.9 g, 13.35 mmol) and PPh3 (4.38 g, 16.70 mmol) in dry THF (110 mL) at 0° C. was added dropwise DIAD (3.37 g, 16.70 mmol) over a period of 5 minutes under a nitrogen atmosphere, then the mixture was stirred at room temperature for 4 hours. Removed the solvent under reduced pressure and then extracted with DCM, the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo and the residue was purified by preparative HPLC separation to afford 3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.3 g, yield 32.4%). MS-ESI (m/z): 640 (M+2)+ (Acq Method: 10-80AB_2 min; Rt: 1.357 min)

Aufarbeitung

  1. customRemoved the solvent under reduced pressure
  2. extractionextracted with DCM
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by preparative HPLC separation

Quellen und Nachweise

ORD-Eintrag
ord-5ca6649f5c814447b4fbfc149626ab43
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09446130B2

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