HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1914005Generated: October 30, 2026
Diisopropylethylamine → tert-Butyl (1-(4-((6-chloro-3-nitropyridin-2-yl)amino)phenyl)cyclobutyl)carbamate
https://huagongshe.com/reaction/1914005
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2,6-Dichloro-3-nitropyridine | HCID 85239 | — |
| Reactant | Carbamic acid, N-(1-(4-aminophenyl)cyclobutyl)-, 1,1-dimethylethyl ester | HCID 56924485 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert-Butyl (1-(4-((6-chloro-3-nitropyridin-2-yl)amino)phenyl)cyclobutyl)carbamate | HCID 58345132 | 75.9% |
Reaction Steps
To a solution of 2,6-dichloro-3-nitropyridine (54 g) in THF (1200 mL), were added ethyl diisopropylamine (1.05 eq.) and tert-butyl[1-(4-aminophenyl)cyclobutyl]carbamate (74 g) at −14° C. and the mixture was warmed up to 25° C. The mixture was stirred for 24 h and diluted with ethyl acetate (1 L) and water (750 mL). The separated organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the residue was solidified with ethyl acetate/hexane (1:1) to give tert-butyl (1-{4-[(6-chloro-3-nitropyridin-2-yl)amino]phenyl}cyclobutyl)carbamate (89 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609688B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-5e475c3545714aa4835a1c8120954fbe |
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| Source note | uspto-grants-2013_12 |
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