Triethyl Phosphate → HCID 86732331, compound
Reaction equation
P(OCC)(OCC)(OCC)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:26]1(=[O:33])[CH2:31][CH2:30][CH2:29][C:28](=[O:32])[CH2:27]1.[F:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42]([NH2:44])=[O:43])=[CH:37][C:36]=1[C:45]([F:48])([F:47])[F:46].[CH:49]([C:51]1[CH:58]=[CH:57][C:54]([C:55]#[N:56])=[CH:53][CH:52]=1)=O>COC(C)(C)C>[C:55]([C:54]1[CH:57]=[CH:58][C:51]([CH:49]([C:27]2[C:28](=[O:32])[CH2:29][CH2:30][CH2:31][C:26]=2[OH:33])[NH:44][C:42]([NH:41][C:38]2[CH:39]=[CH:40][C:35]([F:34])=[C:36]([C:45]([F:46])([F:47])[F:48])[CH:37]=2)=[O:43])=[CH:52][CH:53]=1)#[N:56]Participants
7
Conditions
- Temperature
- 50 °C
Procedure
A mixture of triethyl phosphate (620 μL, 3.66 mmol) and phosphorous pentoxide (346 mg, 2.44 mmol) is heated at 50° C. over night and dilutet with tert-butyl methyl ether (7 mL). Cyclohexane-1,3-dione (513 mg, 4.57 mmol), 1-(4-fluoro-3-(trifluoromethyl)phenyl)urea (677 mg, 3.05 mmol) and 4-formylbenzonitrile (400 mg, 3.05 mmol) are added, and the mixture is heated at 55° C. for 3 h. All volatiles are removed under reduced pressure. The residue is dissolved in methanol, and the mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% formic acid). Yield: 551 mg; ESI mass spectrum [M+H]+=448; Retention time HPLC: 1.04 min (Z018_S04).
Workup
- temperaturethe mixture is heated at 55° C. for 3 h
- customAll volatiles are removed under reduced pressure
- dissolutionThe residue is dissolved in methanol
- customthe mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% formic acid)
- custom1.04 min (Z018_S04)
Sources & evidence
- ORD record
- ord-db5a21c5e28944baa5c97ecb498a2969
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115093B2
Reaction notes
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