N-methyl-2-pyrrolidone → HCID 49779908, compound

HRID 1773249Notes

Reaction equation

[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.CN1C(=O)CCC1.[OH-].[K+].[CH:25]([C:27]1[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH2:35][N:36]2C(=O)C3C(=CC=CC=3)C2=O)=[N:31][CH:32]=1)=[CH2:26]>O>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6]([CH2:26][CH2:25][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][CH2:34][CH2:35][NH2:36])=[N:31][CH:32]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 120 °C

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.005 mol) was taken into NMP (3 mL), and to it was added finely crushed KOH (280 mg, 0.005 mol) and 2-(3-(5-vinylpyridin-2-yl)propyl)isoindoline-1,3-dione (146 mg, 0.005 mol). The reaction was heated at 120° C. for 12 h. The reaction was monitored by LCMS. After 12 h, 2 mL of water was added to the reaction mixture and heated at 120° C. for 12 h. The reaction was monitored by LCMS. After completion of reaction the mixture was cooled and water was added, followed by extraction with EtOAc. The organic extract was dried over sodium sulfate and concentrated under vacuum to yield 800 mg of crude product. 1HNMR (CDCl3, Oxalate salt) d (ppm): 8.17 (s, 1H), 7.22 (s, 1H), 1.18 (d, 1H), 7.15 (d, 1H), 6.95 (m, 2H), 4.20 (t, 2H), 3.70 (s, 2H), 3.0 (t, 2H), 2.90 (t, 2H), 2.80 (t, 2H), 2.70 (t, 2H), 2.58 (s, 3H), 2.40 (s, 3H), 2.37 (m, 2H), 1.80 (t, 2H).

Workup

temperatureheated at 120° C. for 12 h
customAfter completion of reaction the mixture
temperaturewas cooled
extractionfollowed by extraction with EtOAc
extractionThe organic extract
dry with materialwas dried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-50f7462b07e54ba682cf1f6ac818274f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255094B2

Reaction notes

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