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

HRID 1814781Notes

Reaction equation

HRID 1814781 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:28][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([C:45](Cl)=[O:46])[C:34]=1[C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=1.C(OCC)(=O)C>C(Cl)Cl>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:45]([C:33]3[C:34]([C:35]4[CH:40]=[CH:39][C:38]([C:41]([F:42])([F:44])[F:43])=[CH:37][CH:36]=4)=[C:29]([CH3:28])[CH:30]=[CH:31][CH:32]=3)=[O:46])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 110556396-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid chlorideHCID 42609144tert-butyl N-(5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

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′-trifluoromethyl-1,1′-biphenyl-2-carboxylic acid chloride (12.6 mmol) in methylene chloride. 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′-trifluoromethyl-1,1′-biphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-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-973b206b679a44c2a405d8227dbdd3a3
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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