Triethylamine → HCID 45376104, Verbindung

HRID 421400

Reaktionsgleichung

Reaktionsgleichung von HRID 421400
[C:1]([OH:6])(=O)[C@H:2]([CH3:4])[OH:3].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.[CH:37]1([CH2:40][N:41]2[C:49]([N:50]3[CH2:55][CH2:54][NH:53][C@@H:52]([CH3:56])[CH2:51]3)=[N:48][C:47]3[C:42]2=[N:43][C:44]([C:63]2[CH:64]=[N:65][C:66]([NH2:69])=[N:67][CH:68]=2)=[N:45][C:46]=3[N:57]2[CH2:62][CH2:61][O:60][CH2:59][CH2:58]2)[CH2:39][CH2:38]1>C(Cl)Cl.CO.CN(C)C=O>[NH2:69][C:66]1[N:65]=[CH:64][C:63]([C:44]2[N:43]=[C:42]3[C:47]([N:48]=[C:49]([N:50]4[CH2:55][CH2:54][N:53]([C:1](=[O:6])[C@@H:2]([OH:3])[CH3:4])[C@@H:52]([CH3:56])[CH2:51]4)[N:41]3[CH2:40][CH:37]3[CH2:39][CH2:38]3)=[C:46]([N:57]3[CH2:62][CH2:61][O:60][CH2:59][CH2:58]3)[N:45]=2)=[CH:68][N:67]=1

Komponenten

8

Edukt 5

HCID 8471Triethylamine3×HCID 107689L-Lactic Acid3×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride3×HCID 27960291-Hydroxybenzotriazole hydrateHCID 593335285-{9-(Cyclopropylmethyl)-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

Produkt 1

HCID 45376104HCID 45376104, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

L-Lactic acid (27.1 μl, 0.31 mmol), 1-hydroxybenzotriazole monohydrate (39.3 mg, 0.26 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (73.8 mg, 0.38 mmol), and triethylamine (53.6 μl, 0.38 mmol) were added to an N,N-dimethylformamide solution (2.0 ml) of 5-{9-(cyclopropylmethyl)-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (115.6 mg, 0.26 mmol) at room temperature. The resulting mixture was stirred for 20 hours followed by the addition of L-lactic acid (27.1 μl, 0.31 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (73.8 mg, 0.38 mmol), and triethylamine (53.6 μl, 0.38 mmol) and the resulting mixture was stirred for 3 days. L-Lactic acid (27.1 μl, 0.31 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (73.8 mg, 0.38 mmol), and triethylamine (53.6 μl, 0.38 mmol) were further added, the resulting mixture was stirred for 2 days, and then the reaction mixture was poured into methylene chloride-methanol (10:1), washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer silica gel chromatography (double development with methylene chloride:methanol=15:1) to give the title compound (89.7 mg, 67%) as a pale yellow solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 3 days
  2. stirringthe resulting mixture was stirred for 2 days
  3. washwashed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by preparative thin layer silica gel chromatography (double development with methylene chloride:methanol=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-54de923813a84d18a490ba3a9d7be0ca
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097622B2

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