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

HRID 1852899Notes

Reaction equation

HRID 1852899 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.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>C1COCC1.C(OCC)(=O)C.O>[Cl:11][C:4]1[N:3]=[C:2]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH2:29][CH2:30][CH2:31]3)=[CH:24][CH:23]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 56924485Carbamic acid, N-(1-(4-aminophenyl)cyclobutyl)-, 1,1-dimethylethyl ester

Product 1

HCID 58345132tert-Butyl (1-(4-((6-chloro-3-nitropyridin-2-yl)amino)phenyl)cyclobutyl)carbamateYield 75.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

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

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

Sources & evidence

ORD record
ord-59181d173f634c8c9b2cb359e4bede53
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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