Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 6530-09-2 | HCID 18401282 | — |
| Reactant | 5-Fluoro-N-methyl-2-nitrobenzamide | HCID 44203077 | — |
| Reactant | HCID 68176228 | HCID 68176228 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 67115295 | HCID 67115295 | 26.9% |
Reaction Steps
To a mixture of quinuclidin-3-amine hydrochloride (1.06 g, 5.30 mmol) and polymer supported dimethylperhydro-1,3,2-diazaphosphorine (7.0 g, 15.4 mmol) in DMSO (50 mL) was added 5-fluoro-N-methyl-2-nitrobenzamide (Intermediate 3A) (1 g, 5.05 mmol) and reaction heated at 60° C. for 72 hours. The resin was removed by filtration and washed thoroughly with methanol and dichloromethane. The filtrate was purified using a 20 g SCX cartridge followed by trituration with dichloromethane/methanol/diethyl ether to afford N-methyl-2-nitro-5-(quinuclidin-3-ylamino)benzamide (0.41 g, 1.36 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08841289B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-5c6af0e6651d4893922c2bc8eb4fb08b |
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| Source note | uspto-grants-2014_09 |
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