Trifluoroacetic acid → (E)-N-(2-Aminoethyl)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamide

HRID 1503065Notes

Reaction equation

HRID 1503065 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[CH:27]=[C:26](/[CH:28]=[CH:29]/[CH:30]([C:35]2[CH:40]=[C:39]([Cl:41])[C:38]([Cl:42])=[C:37]([Cl:43])[CH:36]=2)[C:31]([F:34])([F:33])[F:32])[CH:25]=[CH:24][C:10]=1[C:11]([NH:13][CH2:14][CH2:15][NH:16]C(=O)OC(C)(C)C)=[O:12]>C(Cl)Cl>[NH2:16][CH2:15][CH2:14][NH:13][C:11](=[O:12])[C:10]1[CH:24]=[CH:25][C:26](/[CH:28]=[CH:29]/[CH:30]([C:35]2[CH:40]=[C:39]([Cl:41])[C:38]([Cl:42])=[C:37]([Cl:43])[CH:36]=2)[C:31]([F:34])([F:32])[F:33])=[CH:27][C:9]=1[Br:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86722550(E)-tert-Butyl 2-(2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamido)ethylcarbamate

Product 1

HCID 86722551(E)-N-(2-Aminoethyl)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamideYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to a stirred solution of (E)-tert-butyl 2-(2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzamido)ethylcarbamate (200 mg, 0.31 mmol) in CH2Cl2 (10 mL) at 0° C. and the reaction mixture was then stirred at ambient temperature for 18 h. The volatiles were evaporated under reduced pressure; water was added to the residue and the mixture extracted with CH2Cl2. The organic layer was washed with brine, dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 1-5% MeOH in CH2Cl2 to afford the title compound as a brown solid (50 mg, 31%): 1H NMR (400 MHz, DMSO-d6) δ 8.56 (bs, 1H), 7.70 (bs, 2H), 7.94-7.91 (m, 3H), 7.62-7.59 (m, 1H), 7.50 (d, J=7.6 Hz, 1H), 7.00 (dd, J=15.6, 9.2 Hz, 1H), 6.77 (d, J=15.6 Hz, 1H), 4.84-4.81 (m, 1H), 3.46-3.41 (m, 2H), 2.95-2.92 (m, 2H); ESIMS m/z 528.72 ([M+H]+); IR (thin film) 3435, 1671, 1113, 722, 555 cm−1.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. additionwater was added to the residue
  3. extractionthe mixture extracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography on silica (100-200 mesh)
  9. washeluting with 1-5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-505a2dc732304cdd9e60b037f6ca1c98
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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