Trifluoroacetic acid → HCID 86666628, compound

HRID 587844Notes

Reaction equation

HRID 587844 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH:20][C:21]([C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[CH:28]([NH:32]C(=O)OC(C)(C)C)[CH2:27][CH2:26]2)=[O:22])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:32][CH:28]1[C:29]2[C:25](=[CH:24][C:23]([C:21]([NH:20][C:4]3[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17])=[CH:8][C:3]=3[CH2:1][CH3:2])=[O:22])=[CH:31][CH:30]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86666629HCID 86666629, compound

Product 1

HCID 86666628HCID 86666628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl (5-{[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-carbamoyl}-2,3-dihydro-1H-inden-1-yl)carbamate (1.3 g) was dissolved in methylene chloride (15 ml), trifluoroacetic acid (1.5 g) was added thereto and then stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure. Water and potassium carbonate were added to neutralize the residue and extracted twice with ethyl acetate. The organic phases were combined, washed with a saturated sodium bicarbonate aqueous solution and water sequentially, and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 1-amino-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]indane-5-carboxamide as a crude product (0.84 g). The crude product was used for the next step without further purification.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionWater and potassium carbonate were added
  3. extractionextracted twice with ethyl acetate
  4. washwashed with a saturated sodium bicarbonate aqueous solution and water sequentially
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-263969c101b546c681c125e3bd74d966
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

Loading…