L-Lactic Acid → (2S)-1-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-1-oxopropan-2-ol

HRID 421379

Reaktionsgleichung

Reaktionsgleichung von HRID 421379
[C:1]([OH:6])(=O)[C@H:2]([CH3:4])[OH:3].O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.FC(F)(F)C(O)=O.[N:37]1([C:43]2[N:51]=[C:50]([C:52]3[CH:53]=[N:54][C:55]([NH2:58])=[N:56][CH:57]=3)[N:49]=[C:48]3[C:44]=2[N:45]=[C:46]([N:64]2[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]2)[N:47]3[CH2:59][C:60]([F:63])([F:62])[F:61])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C(N(CC)CC)C.CN(C)C=O>[NH2:58][C:55]1[N:56]=[CH:57][C:52]([C:50]2[N:49]=[C:48]3[C:44]([N:45]=[C:46]([N:64]4[CH2:69][CH2:68][N:67]([C:1](=[O:6])[C@@H:2]([OH:3])[CH3:4])[CH2:66][CH2:65]4)[N:47]3[CH2:59][C:60]([F:61])([F:63])[F:62])=[C:43]([N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[N:51]=2)=[CH:53][N:54]=1

Komponenten

7

Edukt 4

HCID 107689L-Lactic 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 59333520(2S)-1-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-1-oxopropan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

L-Lactic acid (17 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 5 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 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-30a61032169e45608c535bd88a2856e3
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097622B2

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