2,4,5-Trimethyloxazole → 4-(1,3,3a,4,7,7a-Hexahydro-4,6,7-trimethyl-1,3-dioxo-4,7-epoxy-2H-pyrrolo[3,4-c]pyridin-2-yl)-2-(trifluoromethyl)benzonitrile

HRID 966884Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[O:9]=[C:10]1[CH:14]=[CH:13][C:12](=[O:15])[N:11]1[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]12[O:3][C:4]([CH3:8])([CH:14]3[C:10](=[O:9])[N:11]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:25])([F:27])[F:26])[CH:17]=4)[C:12](=[O:15])[CH:13]31)[C:5]([CH3:7])=[N:6]2

Participants

Conditions

Temperature: 75 °C

Procedure

2,4,5-Trimethyl oxazole (0.48 mL, 4.14 mmol) was dissolved in toluene (2.0 mL) and 4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-2-trifluoromethylbenzonitrile (1.00 g, 3.76 mmol) was added. The reaction mixture was stirred at 75° C. under nitrogen for 2.5 hrs. The solution was cooled to room temperature and the resulting precipitate was filtered and rinsed with toluene to give 0.51 g (35%) of compound 211 as a light grey solid. NMR analysis revelaed that compound 211 was one isomer (exo/endo) however the identity of the isomer could not be determined by NMR analysis. HPLC: 100% at 2.85 min (retention time) (YMC S5 ODS column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm). MS (ES): m/z 378.42 [M+H]+.

Workup

temperatureThe solution was cooled to room temperature
filtrationthe resulting precipitate was filtered
washrinsed with toluene

Sources & evidence

ORD record: ord-e612cb81cdf14cb89115ead5111e1715
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953679B2

Reaction notes

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