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

HRID 1531307Notes

Reaction equation

HRID 1531307 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18]([C:20]3[C:21]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:19])[CH:14]=2)[CH2:9]1)(C)(C)C>C(O)=O>[NH2:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:17][C:18]([C:20]3[C:21]([C:27]4[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=4)=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[O:19])[CH:14]=2)[CH2:9]1

Participants

3

Reactant 1

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

Product 1

HCID 224988156-Methyl-4'-trifluoromethylbiphenyl-2-carboxylic acid (2-amino-indan-5-yl)-amide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of {5-[(6-methyl-4′-trifluoromethylbiphenyl-2-carbonyl)-amino]-indan-2-yl}-carbamic acid tert-butyl ester (5.19 g,10.5 mmol) in formic acid (40 mL) is heated to 40° C. with stirring. After 3 h, the reaction mixture is cooled to room temperature and stirring is continued for 16 h. The reaction mixture is concentrated under reduced pressure and the resulting oil dissolved in ethyl acetate. The organic layer is washed with 8% NaHCO3 solution until the aqueous layer remains basic at which point a precipitate forms in the organic layer. The precipitate is collected by filtration to give 6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid (2-amino-indan-5-yl)-amide.

Workup

  1. stirringstirring
  2. waitis continued for 16 h
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. dissolutionthe resulting oil dissolved in ethyl acetate
  5. washThe organic layer is washed with 8% NaHCO3 solution until the aqueous layer
  6. filtrationThe precipitate is collected by filtration

Sources & evidence

ORD record
ord-2b0875f01446478cbd93c4bbd0f1b16a
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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