Glycolic Acid → 2-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-2-oxoethanol

HRID 1876567

Reaktionsgleichung

Reaktionsgleichung von HRID 1876567
[OH:1][CH2:2][C:3]([OH:5])=O.O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.FC(F)(F)C(O)=O.[N:36]1([C:42]2[N:50]=[C:49]([C:51]3[CH:52]=[N:53][C:54]([NH2:57])=[N:55][CH:56]=3)[N:48]=[C:47]3[C:43]=2[N:44]=[C:45]([N:63]2[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)[N:46]3[CH2:58][C:59]([F:62])([F:61])[F:60])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(N(CC)CC)C.CN(C)C=O>[NH2:57][C:54]1[N:55]=[CH:56][C:51]([C:49]2[N:48]=[C:47]3[C:43]([N:44]=[C:45]([N:63]4[CH2:68][CH2:67][N:66]([C:3](=[O:5])[CH2:2][OH:1])[CH2:65][CH2:64]4)[N:46]3[CH2:58][C:59]([F:60])([F:62])[F:61])=[C:42]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[N:50]=2)=[CH:52][N:53]=1

Komponenten

7

Edukt 4

HCID 757Glycolic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866419965-[6-Morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetateHCID 178526939HCID 178526939, Verbindung

Produkt 1

HCID 593335412-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-2-oxoethanolAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

2-Hydroxyacetic acid (15 mg, 0.19 mmol), hydroxybenzotriazole hydrate (37 mg, 0.19 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (37 mg, 0.19 mmol), dimethylformamide (3 ml), and triethylamine (100 μl) were added to 5-[6-morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate (120 mg, 0.17 mmol) and the resulting mixture was stirred for 4 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=19:1) to give the title compound (70 mg) as a colorless solid.

Aufarbeitung

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (chloroform:methanol=19:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b70cad33e4f48fbac966bbd9c322c82
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309546B2

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