HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1914005
Notes
Print preview

Reaction equation

HRID 1914005 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent
HCID 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-5e475c3545714aa4835a1c8120954fbe
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609688B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes