Hydrochloric Acid → HCID 86653078, compound

HRID 339131

Reaction equation

HRID 339131 reaction equation
[O:1]=[C:2]([NH:22][CH:23]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=1)[C:24]([F:27])([F:26])[F:25])/[CH:3]=[CH:4]/[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH:14]C(=O)OC(C)(C)C)[CH2:9][CH2:8]2.Cl.O>O1CCOCC1>[NH2:14][CH:10]1[C:11]2[C:7](=[CH:6][C:5](/[CH:4]=[CH:3]/[C:2]([NH:22][CH:23]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=3)[C:24]([F:25])([F:26])[F:27])=[O:1])=[CH:13][CH:12]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86653077tert-butyl {5-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]-2,3-dihydro-1H-inden-1-yl}carbamate

Product 1

HCID 86653078HCID 86653078, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.2 g of tert-butyl {5-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-amino)prop-1-en-1-yl]-2,3-dihydro-1H-inden-1-yl}carbamate were dissolved in 40 ml of dioxane and admixed with 10 ml of semisaturated hydrochloric acid, and stirred at room temperature overnight. The reaction mixture was admixed with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 1.5 g of (2E)-3-(1-amino-2,3-dihydro-1H-inden-5-yl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]-ethyl}-acrylamide (82%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-97bd1eda03cd4c65b483de5236d2ebf3
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Linked notes

Loading…