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

HRID 1531269Notes

Reaction equation

HRID 1531269 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.[F:28][C:29]([F:46])([F:45])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[C:37]([C:42](Cl)=[O:43])=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:32][CH:31]=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:42]([C:37]3[C:36]([C:33]4[CH:34]=[CH:35][C:30]([C:29]([F:28])([F:45])[F:46])=[CH:31][CH:32]=4)=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:43])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 110660004'-(Trifluoromethyl)-[1,1'-biphenyl]-2-carbonyl chlorideHCID 42609144tert-butyl N-(5-amino-2,3-dihydro-1H-inden-2-yl)carbamate

Product 1

HCID 70184229{5-[(4'-Trifluoromethylbiphenyl-2-carbonyl)-amino]indan-2-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the title C compound ((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 0.5 M solution of the title D compound (4′-trifluoromethyl-2-biphenyl carboxylic acid chloride, 12.6 mmol) in methylene chloride (25.3 mL). After stirring 16 h, the reaction mixture is poured into ethyl acetate and washed with 1N HCl, 8% NaHCO3 solution, and brine. The organic layer is dried (MgSO4) and concentrated under reduced pressure to give a solid. Recrystallization from toluene gives {5-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]-indan-2-yl}-carbamic acid tert-butyl ester in two crops; mp 198-201° C. MS (ES+), m/z 514 (M+NH+4).

Workup

  1. washwashed with 1N HCl, 8% 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-f7563fe22130482886cd4ed1bb880572
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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