Urea → HCID 178429231, compound

HRID 227723Notes

Reaction equation

HRID 227723 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12](=[O:17])[CH2:13][C:14](=O)[CH3:15])[CH:9]=2)[NH:4][N:3]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.[NH2:27][C:28]([NH2:30])=[O:29].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>CC#N>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:13]3[CH:23]([C:22]4[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=4)[NH:27][C:28](=[O:29])[NH:30][C:14]=3[CH3:15])=[O:17])[CH:9]=2)[NH:4][N:3]=1

Participants

6

Reactant 4

HCID 1176UreaHCID 680234-FluorobenzaldehydeHCID 2733225Ytterbium triflateHCID 178468064HCID 178468064, compound

Product 1

HCID 178429231HCID 178429231, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

The product of Step (c) (330 mg, 1.11 mmol, 1 equiv), 4-fluorobenzaldehyde (120 uL, 1.13 mmol, 1.00 equiv), urea (100 mg, 1.67 mmol, 1.67 equiv), and Ytterbium triflate (70 mg, 0.12 mmol, 0.10 equiv) were combined in CH3CN (6 mL). The reaction vessel was sealed and heated to 100° C. for 18 hours. The reaction was cooled to room temperature and the precipitate was collected by filtration. The solid was washed with Et2O/CH3CN several times, then purified by preparative LC-MS to afford 40 mg (8%) of a white solid. 1H NMR (400 MHz, d6-DMSO) 13.3 (s, 1H), 9.69 (s, 1H), 8.77 (s, 1H), 7.96 (s, 1H), 7.62 (m, 1H), 7.48 (s, 2H), 7.35 (m, 2H), 7.17 (m, 2H), 5.43 (m, 1H), 2.07 (s, 3H).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe precipitate was collected by filtration
  4. washThe solid was washed with Et2O/CH3CN several times
  5. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-5141fa65610f4ff09271cae664d215cb
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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