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

HRID 1013493Notes

Reaction equation

HRID 1013493 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)Cl>N1C=CC=CC=1>[C:29]([O:28][C:27]([NH:26][C:16]1[CH:17]=[CH:18][C:19]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[CH:20][C:15]=1[NH:14][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])=[O:33])([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 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 1049PyridineSolvent

Procedure

Methyl 4-(chlorocarbonyl)benzoate (1.40 g, 7.07 mmol) and tert-butyl [2-amino-4-(2-thienyl)phenyl]carbamate (2.05 g, 7.07 mmol) were combined in pyridine (10 mL) and stirred at room temperature for 18 h. The reaction mixture was poured into 3:1 CHCl3:MeOH, washed with 2 N HCl and 2 N NaOH, dried (Na2SO4), and evaporated to give the desired product as a colorless solid. MS: cal'd 475 (MNa+), exp 475 (MNa+).

Workup

  1. washMeOH, washed with 2 N HCl and 2 N NaOH
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-c0c8d15338344495a5a8e50f176f643e
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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