Methyl 4-(chlorocarbonyl)benzoate → Methyl 4-[({2-[(tert-butoxycarbonyl)amino]-5-thien-2-ylphenyl}amino)carbonyl]benzoate

HRID 1013516Notes

Reaction equation

HRID 1013516 reaction equation
Cl[C:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3].[NH2:14][C:15]1[CH:20]=[C:19]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)[CH:18]=[CH:17][C:16]=1[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30]>C(Cl)Cl>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][C:4]([C:2]([NH:14][C:15]2[CH:20]=[C:19]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH:18]=[CH:17][C:16]=2[NH:26][C:27]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:33])=[O:3])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 57607810Methyl 4-[({2-[(tert-butoxycarbonyl)amino]-5-thien-2-ylphenyl}amino)carbonyl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-(chlorocarbonyl)benzoate (0.75 g, 3.79 mmol) and anhydrous DCM (0.25 M) was treated with tert-butyl 2-amino-4-thien-2-ylphenylcarbamate (1.0 g, 3.44 mmol). The resulting solution was stirred at ambient temperature for 14 hours. The reaction mixture was quenched with a solution of aqueous NaOH (1M) and partitioned between ethyl acetate and water. The organic layer was washed with water, saturated aqueous sodium bicarbonate, brine, dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was carried on without further purification.

Workup

  1. customThe reaction mixture was quenched with a solution of aqueous NaOH (1M)
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was carried on without further purification

Sources & evidence

ORD record
ord-d8845d5769aa473fbb6b0accef49d1fe
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

Loading…