Urea → HCID 57755913, compound

HRID 227718Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

The product of Step (d) (41.0 mg, 0.276 mmol, 1.0 equiv) was dissolved in CH3CN (1 mL) and diketene (0.021 mL, 0.276 mmol, 1.0 equiv) was added. The reaction was heated to 80° C. for 2 hours, then cooled to room temperature and concentrated. The residue was dissolved in CH3CN (1 mL). 4-Fluorobenzaldehyde (0.030 mL, 0.276 mmol, 1.00 equiv), urea (25 mg, 0.41 mmol, 1.5 equiv), and ytterbium triflate (17 mg, 0.028 mmol, 0.10 equiv) and heated to 80° C. for 3 hours. The reaction was cooled to room temperature and water was added. The precipitate was collected by filtration and washed alternately with CH3CN and Et2O. The residue was purified by reverse phase HPLC (740% CH3CN/5 mM NH4HCO3, 19×50 mm Xterra Prep MS over 8 min) to provide 3 mg (3%) of the title compound. MS (ES+) m/e 384 [M+H].

Workup

temperaturecooled to room temperature
concentrationconcentrated
dissolutionThe residue was dissolved in CH3CN (1 mL)
temperatureThe reaction was cooled to room temperature
filtrationThe precipitate was collected by filtration
washwashed alternately with CH3CN and Et2O
customThe residue was purified by reverse phase HPLC (740% CH3CN/5 mM NH4HCO3, 19×50 mm Xterra Prep MS over 8 min)

Sources & evidence

ORD record: ord-5511ecf4142c4108b0f328f25724d995
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560467B2

Reaction notes

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