HCID 68736952, compound → HCID 86632921, compound

HRID 1628581Notes

Reaction equation

HRID 1628581 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].Cl.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[CH:29]([OH:34])[C:30](=N)OC>C(O)C.C(=O)([O-])O.[Na+].O>[NH2:1][C:2]1[C:3]2[N:9]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[C:30]([CH:29]([C:23]3[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=3[Cl:21])[OH:34])=[N:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 68736952HCID 68736952, compoundHCID 86632920HCID 86632920, compound

Product 1

HCID 86632921HCID 86632921, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of tert-butyl {2-[(2,6-diaminophenyl)amino]ethyl}carbamate (5.00 g, 18.8 mmol) in ethanol (38 mL) was added methyl 2-(2,4-dichlorophenyl)-2-hydroxyethanimidoate hydrochloride (5.59 g, 20.7 mmol) at room temperature. After 12 h, the reaction mixture was diluted with aqueous sodium hydrogen carbonate and water. The resultant mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate to give the title compound as a brown amorphous solid (8.46 g, 18.7 mmol, 99%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-0f15372b503d4d13a5a7d0bb63386d24
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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