UC2288 synthesis
- Product Name:UC2288
- CAS Number:1394011-91-6
- Molecular formula:C20H18ClF6N3O2
- Molecular Weight:481.82
![Urea, N-[4-chloro-3-(trifluoromethyl)phenyl]-N'-(trans-4-hydroxycyclohexyl)-](/CAS/20210111/GIF/1394011-78-9.gif)
1394011-78-9
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Yield:1394011-91-6 83%
Reaction Conditions:
Stage #1: trans-1-(4-chloro-3-trifluoromethylphenyl)-3-(4-hydroxycyclohexyl)ureawith sodium hydride in N,N-dimethyl-formamide;mineral oil at 0; for 0.166667 h;Inert atmosphere;
Stage #2: 2-chloro-5-trifluoromethylpyridine in N,N-dimethyl-formamide;mineral oil at 0 - 20;Inert atmosphere;
Steps:
10
To a solution of 07086 from Example 4 (0.17 g, 0.5 mmol) in DMF (5 mL) was added 60% sodium hydride in oil (0.03 g, 0.75 mmol) portionwise at 0 °C. After 10 min, 2- chloro-5-(trifluoromethyl)pyridine (0.14 g, 0.75 mmol) was added. The reaction mixture was allowed to slowly warm to room temperature overnight. The reaction was quenched by adding water and the resulting white precipitates were collected and washed with water. The collected solid was recrystallized from methanol to give the title compound, 0.2 g (83%) as a white solid, mp 176.5-177.9 °C. NMR (300 MHz, OMSO-d6): δ 8.82 (s, 1H), 8.58-8.54 (m, 1H), 8.08-8.06 (m, 1H), 8.04 (dd, J= 9 and 3 Hz, 1H), 7.54-7.52 (m, 2H), 6.96 (d, J= 9 Hz, 1H), 6.30 (d, J= 8 Hz, 1H), 5.13-4.99 (m, 1H), 3.64-3.48 (m, 1H), 2.15-1.89 (m, 4H), 1.63-1.30 (m, 4H).
References:
WO2012/112570,2012,A1 Location in patent:Page/Page column 50
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