1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 56646359, compound

HRID 1048973Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10](=O)[C:11]2[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[N:13][CH:12]=2)=[C:4]([NH:22][CH3:23])[CH:3]=1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[N:9]=[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[C:17]([F:20])([F:19])[F:18])[N:22]([CH3:23])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To the solution of compound N-(4-chloro-5-fluoro-2-(methylamino) phenyl)-4-(tri-fluoromethyl) nicotinamide (0.1 g, 0.0028 mol) in DMA (5 ml) was added DBU (0.05 g, 0.0037 mol). Reaction mixture was heated at 140° C. for 24 h. Reaction mass was quenched with ice water and layers were separated. The aqueous layer was extracted with EtOAc (3×10 ml). The combined organic extracts were washed with brine dried over Na2SO4 and concentrated to get crude product which was purified by column chromatography to provide 6-chloro-5-fluoro-1-methyl-2-[4-(trifluoromethyl)pyridin-3-yl]-1H-benzimidazole 335; as a white colored solid. 1H NMR (400 MHz, DMSO-d6), δ: 9.11-9.09 (d, J=5.2 Hz, 1H), 9.03 (s, 1H), 8.07-8.04 (m, 2H), 7.82-7.79 (d, J=10 Hz, 1H), 3.65 (s, 3H). MS (M+1): 330.12, Purity 99.52%.

Workup

customReaction mixture
customReaction mass
customwas quenched with ice water and layers
customwere separated
extractionThe aqueous layer was extracted with EtOAc (3×10 ml)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customto get crude product which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-a054c56f5f7f43cfbf0473042e7f08f4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382226B2

Reaction notes

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