Water → 1,1-Dimethylethyl N-[2-[[[(4-aminophenyl)amino]carbonyl]amino]ethyl]carbamate

HRID 527387Notes

Reaction equation

HRID 527387 reaction equation
N1CCCCC1.[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:23][CH:22]=1)=[O:19])=[O:13])([CH3:10])([CH3:9])[CH3:8].O>CN(C=O)C>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:18]([NH:17][CH2:16][CH2:15][NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])=[O:19])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 67121345HCID 67121345, compound

Product 1

HCID 671212751,1-Dimethylethyl N-[2-[[[(4-aminophenyl)amino]carbonyl]amino]ethyl]carbamateYield 117.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Piperidine (9.68 mL, 97.75 mmol, 5.0 eq) was added at room temperature to a stirred solution of N-(4-[({2-[(tert-butoxy)carbonylamino]ethyl)amino)carbonylamino]phenyl}(fluoren-9-ylmethoxy)carboxamide (10.10 g, 19.55 mmol, 1.0 eq) in DMF (140 mL). After 2 hours stirring at room temperature, water was added to the reaction mixture and precipitation occurred. The resulting mixture was filtered, and the liquid phase was concentrated to afford 6.75 g of the expected product as an orange oil:

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe liquid phase was concentrated

Sources & evidence

ORD record
ord-c4162af2e29847e5a7480d4efb328afa
Source dataset
uspto-grants-2016_05
Patent number
US09346799B2

Reaction notes

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