HCID 697349, compound → HCID 58007497, compound

HRID 1094339Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[CH3:14][N:15]1[C:19]2[CH:20]=[CH:21][C:22]([N+]([O-])=O)=[CH:23][C:18]=2[N:17]([CH3:27])[C:16]1=[O:28]>CO.[Pd]>[CH3:27][N:17]1[C:18]2[CH:23]=[CH:22][C:21]([NH:11][CH2:10][CH2:9][C:6]3[CH:7]=[N:8][C:3]([C:2]([F:12])([F:1])[F:13])=[CH:4][CH:5]=3)=[CH:20][C:19]=2[N:15]([CH3:14])[C:16]1=[O:28]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (6-trifluoromethyl-pyridin-3-yl)-acetonitrile (223 mg, 1.21 mmol, prepared as per example 1, step 1) and 1,3-dimethyl-5-nitro-1,3-dihydro-benzoimidazol-2-one (240 mg, 2.41 mmol, commercially available) in MeOH (10 mL) was treated with NH4OAc (13.00 mmol) and 10% Pd/C (200 mg) and stirred at 60° C. for 72 h. Filtration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (216 mg, 25%) as a light yellow oil. MS m/e: 351.1 [M+H]+.

Workup

filtrationFiltration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record: ord-5753df0cc2d6408783fe4d9c350c63ed
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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