1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22051050, compound

HRID 1867136Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].C1CCN2C(=NCCC2)CC1.[F:22][C:23]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:24]=1[CH2:25]Br>CN1C(=O)CCC1>[Cl:1][C:2]1[C:3](=[O:10])[NH:4][C:5]([CH3:9])=[CH:6][C:7]=1[O:8][CH2:25][C:24]1[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:23]=1[F:22]

Participants

Conditions

Temperature: 80 °C

Procedure

3-Chloro-4-hydroxy-6-methyl-1H-pyridin-2-one (19.2 g, 0.12 mol) and DBU (19.9 mL, 0.13 mol) were dissolved in 70 mL of NMP. 2,4-Difluorobenzylbromide (17 mL, 0.13 mol) was added dropwise and the reaction was heated at 80° C. for 6 hours. The reaction was cooled to room temperature, the solid was filtered, and washed with NMP and hexanes. The solid was dried in a vacuum oven overnight to give a white solid (4.4 g, 13%): 1H NMR (300 MHz, DMSO-d6) δ 11.88 (br s, 1H), 7.63 (app q, J=9 Hz, 1H), 7.33 (app t, J=10 Hz, 1H), 7.16 (app t, J=9 Hz, 1H), 6.37 (s, 1H), 5.24 (s, 2H), 2.20 (s, 3H).

Workup

temperatureThe reaction was cooled to room temperature
filtrationthe solid was filtered
washwashed with NMP and hexanes
customThe solid was dried in a vacuum oven overnight

Sources & evidence

ORD record: ord-5a98f5a8a5754c82ade058d7cf738959
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629363B2

Reaction notes

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