Diisopropylethylamine → 1-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-pyrrolidinone

HRID 15880Notes

Reaction equation

C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=3)[NH2:32])[CH2:23][CH2:22]2)[N:12]=1.CS([O:40][CH2:41][CH2:42][C:43]1C=CC=C(N2CCCC2=O)[CH:44]=1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N:21]2[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][C:29]3[CH:30]=[C:31]([N:32]4[CH2:44][CH2:43][CH2:42][C:41]4=[O:40])[CH:33]=[CH:34][CH:35]=3)[CH2:25][CH2:26]2)[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N,N-Diisopropylethylamine (0.23 mL) was added to a solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (0.05 g) and 2-[3-(2-oxo-1-pyrrolidinyl)phenyl]ethyl methanesulfonate (0.071 g) in dimethylformamide (1 mL) and the resulting mixture was heated to 100° C. for 18 hours, then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL), a mixture of water and brine (1:1, 2×50 mL) and brine (50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with methanol-ethyl acetate (90:10) affording the title compound in 77% yield (0.07 g).

Workup

temperaturecooled to room temperature
washwashed with water (50 mL)
additiona mixture of water and brine (1:1, 2×50 mL) and brine (50 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude was purified by flash chromatography on silica gel
washeluting with methanol-ethyl acetate (90:10)

Sources & evidence

ORD record: ord-ab2a73d614ec448dbd23ae70fa71a9b4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732600B2

Reaction notes

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