N-methyl-2-pyrrolidone → HCID 59333538, compound
Reaction equation
[CH:1]([N:4](C(C)C)CC)(C)C.[CH3:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=O.[NH2:17][C:18]1[N:23]=[CH:22][C:21]([C:24]2[N:32]=[C:31]3[C:27]([N:28]=[C:29](Cl)[N:30]3[CH2:33][C:34]([F:37])([F:36])[F:35])=[C:26]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[N:25]=2)=[CH:20][N:19]=1>O>[CH2:14]([C@H:13]1[NH:4][CH2:1][CH2:10][N:11]([C:29]2[N:30]([CH2:33][C:34]([F:35])([F:37])[F:36])[C:31]3[C:27]([N:28]=2)=[C:26]([N:39]2[CH2:40][CH2:41][O:42][CH2:43][CH2:44]2)[N:25]=[C:24]([C:21]2[CH:22]=[N:23][C:18]([NH2:17])=[N:19][CH:20]=2)[N:32]=3)[CH2:12]1)[CH3:15]Participants
Conditions
- Temperature
- 100 °C
Procedure
Diisopropylethylamine (1.91 ml, 10.98 mmol) was added to an N-methyl-2-pyrrolidone suspension (5 ml) of 2-(R)-ethylpiperazine-2-hydrochloride (751 mg) and 2-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine (506 mg, 1.22 mmol) and the resulting mixture was heated at 100° C. and stirred for 5 days. Water was added to the reaction mixture and the resulting mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with water and saturated brine, and dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10) to give the title compound (562 mg) as a pale yellow solid.
Workup
- extractionthe resulting mixture was extracted twice with ethyl acetate
- washwashed with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationthe mixture was filtrated
- concentrationthe filtrate was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10)
Sources & evidence
- ORD record
- ord-92c992c3acef4af3b0950e8838115884
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097622B2
Reaction notes
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