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Tetrahydrofuran → 4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-cis-2,6-dimethylpiperazine-1-carboaldehyde

HRID 1876606
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1876606
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:10]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:11]3[C:16]([N:17]=2)=[C:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:14]=[C:13]([C:24]2[CH:25]=[N:26][C:27]([NH2:30])=[N:28][CH:29]=2)[N:12]=3)[CH2:3]1.[O:36]1CCC[CH2:37]1.CN(CCS(O)(=O)=O)C>C(Cl)Cl>[NH2:30][C:27]1[N:28]=[CH:29][C:24]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[C:9]([N:4]4[CH2:3][C@@H:2]([CH3:1])[N:7]([CH:37]=[O:36])[C@@H:6]([CH3:8])[CH2:5]4)[N:10]3[CH2:31][C:32]([F:35])([F:34])[F:33])=[C:15]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:14]=2)=[CH:25][N:26]=1
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Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 2370422-(Dimethylamino)ethanesulfonic acid2×HCID 453780145-[8-(cis-3,5-dimethylpiperazin-1-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine

Produkt 1

HCID 593335684-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]-cis-2,6-dimethylpiperazine-1-carboaldehydeAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-[8-(cis-3,5-Dimethylpiperazin-1-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine (101.7 mg, 0.21 mmol) were added to a tetrahydrofuran solution (5.0 ml) of 1H-benzotriazole-1-carboxyaldehyde (33.8 mg, 0.21 mmol) at room temperature and the resulting mixture was stirred for 1 day. 1H-Benzotriazole-1-carboxyaldehyde (5.1 mg, 0.03 mmol) was added, the resulting mixture was further stirred for 1 day, and then the reaction mixture was poured into methylene chloride and washed with a 2 N aqueous sodium hydroxide solution. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to give the title compound (98.0 mg, 91%) as a pale yellow solid.

Aufarbeitung

  1. stirringthe resulting mixture was further stirred for 1 day
  2. washwashed with a 2 N aqueous sodium hydroxide solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationthe mixture was filtrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e3d64138d0924169b374e03691d343e0
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08309546B2

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