Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 68763036 | HCID 68763036 | — |
| Product | HCID 70937253 | HCID 70937253 | 44% |
Reaction Steps
Acetyl chloride (0.10 ml, 1.41 mmol) was added to a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-[(trimethyl-λ5-phosphanylidene)amino]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.11 g, 0.16 mmol) in CH2Cl2 (1.0 ml) and the reaction mixture was stirred at 45° C. for 1 h. Sat'd aqueous NaHCO3 was added and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography (0-40% EtOAc/hexanes) to provide the title compound (0.047 g, 44%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.32-7.35 (m, 1H) 7.28-7.32 (m, 2H) 7.19 (t, J=6.04 Hz, 1H) 7.13 (t, J=2.01 Hz, 1H) 7.01 (s, 1H) 5.56 (s, 2H) 4.67 (d, J=6.13 Hz, 2H) 3.55-3.63 (m, 2H) 2.30 (s, 6H) 0.80-0.89 (m, 2H)-0.04 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08304419B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-4c001ef74680427c82f41e556900fc59 |
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| Source note | uspto-grants-2012_11 |
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