Ethyl Acetate → {5-[(6-Methyl-4'-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester

HRID 1531306Notes

Reaction equation

HRID 1531306 reaction equation
[C:1]([O:5][C:6](=[O:8])[NH2:7])([CH3:4])([CH3:3])[CH3:2].C([N:12]([CH:15]([CH3:17])[CH3:16])CC)(C)C.[CH3:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([C:35](Cl)=[O:36])[C:24]=1[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1.C(O[CH2:42][CH3:43])(=O)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:8])[NH:7][CH:43]1[CH2:42][C:3]2[C:1](=[CH:2][CH:17]=[C:15]([NH:12][C:35]([C:23]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[C:19]([CH3:18])[CH:20]=[CH:21][CH:22]=3)=[O:36])[CH:16]=2)[CH2:4]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 77922tert-Butyl carbamateHCID 81531DiisopropylethylamineHCID 110556396-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid chloride

Product 1

HCID 69700046{5-[(6-Methyl-4'-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-indan-2-yl)-carbamic acid tert-butyl ester (12.5 mmol) in methylene chloride (75 mL) is added diisopropylethyl amine (3.3 g, 25 mmol) followed by a solution of 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid chloride in methylene chloride (See Example 14, 12.6 mmol). After stirring 16 h, the reaction mixture is poured into ethyl acetate and washed with 1N HCl, NaHCO3 solution, and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give a solid. Recrystallization from toluene gives {5-[(6-methyl-4′-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid terf-butyl ester.

Workup

  1. washwashed with 1N HCl, NaHCO3 solution, and brine
  2. dry with materialThe organic layer is dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid
  5. customRecrystallization from toluene

Sources & evidence

ORD record
ord-9335f3caa7914b8d86d3d86a53dad3e1
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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