1H-Benzotriazole-1-carboxaldehyde → 4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazine-1-carboaldehyde

HRID 421382

Reaktionsgleichung

Reaktionsgleichung von HRID 421382
N1([CH:10]=[O:11])C2C=CC=CC=2N=N1.FC(F)(F)C(O)=O.[N:19]1([C:25]2[N:33]=[C:32]([C:34]3[CH:35]=[N:36][C:37]([NH2:40])=[N:38][CH:39]=3)[N:31]=[C:30]3[C:26]=2[N:27]=[C:28]([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[N:29]3[CH2:41][C:42]([F:45])([F:44])[F:43])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O1CCCC1.C(OCC)(=O)C>[NH2:40][C:37]1[N:36]=[CH:35][C:34]([C:32]2[N:31]=[C:30]3[C:26]([N:27]=[C:28]([N:46]4[CH2:47][CH2:48][N:49]([CH:10]=[O:11])[CH2:50][CH2:51]4)[N:29]3[CH2:41][C:42]([F:44])([F:43])[F:45])=[C:25]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[N:33]=2)=[CH:39][N:38]=1

Komponenten

5

Edukt 2

HCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 866419965-[6-Morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate

Produkt 1

HCID 593334934-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazine-1-carboaldehydeAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Benzotriazole-1-carboaldehyde (55 mg, 0.38 mmol) was dissolved in tetrahydrofuran (10 ml) followed by the addition of 5-[6-morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate (200 mg, 0.29 mmol). The resulting mixture was stirred for 20 minutes and the reaction mixture was diluted with ethyl acetate, washed with 1 M sodium hydroxide and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (chloroform:methanol=19:1) to give a white solid (80 mg, 56%).

Aufarbeitung

  1. washwashed with 1 M sodium hydroxide and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (chloroform:methanol=19:1)

Quellen und Nachweise

ORD-Eintrag
ord-1f2504b763a54f5792290dba9c3f8777
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097622B2

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