tert-Butyl acrylate → HCID 66678183, compound

HRID 2404339Notes

Reaction equation

[CH:1]([NH:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10])([CH3:3])[CH3:2].[C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[CH:15]=[CH2:16].C1CCN2C(=NCCC2)CC1>O>[C:9]([C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:16][CH2:15][C:14]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])#[N:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-[(isopropylamino)methyl]benzonitrile (5.7 g, 32.7 mmol), tert-butyl acrylate (4.78 ml, 32.7 mmol) and DBU (5.0 ml, 32.7 mmol) was heated neat at 80° C. for 24 hours. The reaction mixture was diluted with water and extracted with DCM. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. After purification by chromatography (silica, pet ether/EtOAc), the title compound was obtained as a colorless oil. 1H NMR (DMSO-d6, 400 MHz) δ 7.73 (s, 1H,), 7.67 (d, J=7.7 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H), 7.49 (t, J=7.7 Hz, 1H), 3.56 (s, 2H), 2.75 (m, 1H), 2.62 (t, J=6.5 Hz, 2H), 2.25 (t, J=6.4 Hz, 2H), 1.39 (s, 9H), 0.83 (d, J=8.8 Hz, 6H).

Workup

extractionextracted with DCM
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customAfter purification by chromatography (silica, pet ether/EtOAc)

Sources & evidence

ORD record: ord-463a952000b04fb0aca6cafe53ce7431
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802704B2

Reaction notes

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