Diisopropylethylamine → tert-Butyl (1-(4-((6-chloro-3-nitropyridin-2-yl)amino)phenyl)cyclobutyl)carbamate

HRID 1914005Notes

Reaction equation

Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.C(N(C(C)C)C(C)C)C.[C:21]([O:25][C:26](=[O:39])[NH:27][C:28]1([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:31][CH2:30][CH2:29]1)([CH3:24])([CH3:23])[CH3:22]>C1COCC1.C(OCC)(=O)C.O>[Cl:11][C:4]1[N:3]=[C:2]([NH:38][C:35]2[CH:36]=[CH:37][C:32]([C:28]3([NH:27][C:26](=[O:39])[O:25][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:29][CH2:30][CH2:31]3)=[CH:33][CH:34]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 25 °C

Procedure

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).

Workup

washThe separated organic phase was washed with brine
dry with materialdried over anhydrous Na2SO4
customThe solvent was removed

Sources & evidence

ORD record: ord-5e475c3545714aa4835a1c8120954fbe
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609688B2

Reaction notes

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