N-methyl-2-pyrrolidone → HCID 59333558, compound

HRID 421383Notes

Reaction equation

HRID 421383 reaction equation
C(N(C(C)C)CC)(C)C.CN1CCCC1=O.[CH2:17]([C@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][NH:20]1)[CH3:18].[NH2:25][C:26]1[N:31]=[CH:30][C:29]([C:32]2[N:40]=[C:39]3[C:35]([N:36]=[C:37](Cl)[N:38]3[CH2:41][C:42]([F:45])([F:44])[F:43])=[C:34]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)[N:33]=2)=[CH:28][N:27]=1>O>[CH2:17]([C@@H:19]1[NH:20][CH2:21][CH2:22][N:23]([C:37]2[N:38]([CH2:41][C:42]([F:43])([F:45])[F:44])[C:39]3[C:35]([N:36]=2)=[C:34]([N:47]2[CH2:48][CH2:49][O:50][CH2:51][CH2:52]2)[N:33]=[C:32]([C:29]2[CH:28]=[N:27][C:26]([NH2:25])=[N:31][CH:30]=2)[N:40]=3)[CH2:24]1)[CH3:18]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 11240458(2S)-2-EthylpiperazineHCID 593335342-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine

Product 1

HCID 59333558HCID 59333558, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Diisopropylethylamine (1.48 ml, 8.49 mmol) was added to an N-methyl-2-pyrrolidone suspension (4 ml) of 2-(S)-ethylpiperazine 2 hydrochloride (529 mg, 2.83 mmol) and 2-(2-aminopyrimidin-5-yl)-8-chloro-6-(morpholin-4-yl)-9-(2,2,2-trifluoroethyl)-9H-purine (391 mg, 0.94 mmol) and the resulting mixture was stirred at 100° C. for 4 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 (379 mg) as a pale yellow solid.

Workup

  1. extractionthe resulting mixture was extracted twice with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationthe mixture was filtrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography (chloroform:methanol=97:3 to 90:10)

Sources & evidence

ORD record
ord-0844ea31597c492582e7eb2b58ed164b
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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