Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 4-Aminobenzonitrile | HCID 13396 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 68816689 | HCID 68816689 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68814957 | HCID 68814957 | 188.9% |
Reaction Steps
To a suspension of the chloro intermediate (0.382 mmol) in 3 mL CH3CN at rt, was added DIEA (0.133 mL, 0.764 mmol), 4-aminobenzonitrile (67.7 mg, 0.573 mmol) and 1 mL CH2Cl2. The mixture was stirred at 50° C. for 3 h, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (O to 50% EtOAc/hexanes gradient) to afford 225 mg of Intermediate 175.3 as a colorless oil. LCMS (4 min gradient, 50 to 100% B, A=95% H2O/5% CH3CN/0.1% TFA, B=95% CH3CN/5% H2O/0.1% TFA) RT=5.20 min, 623.13 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07576098B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-288a3cbde76046238bf7ed3472f2595a |
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| Source note | uspto-grants-2009_08 |
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