Trifluoroacetic acid → HCID 22177252, compound

HRID 1797166Notes

Reaction equation

HRID 1797166 reaction equation
C(OC(=O)[N:7]([C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1)[CH2:8][CH2:9][NH:10][CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1)[CH2:13][CH:14]=[CH2:15])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:29][C:27]1[CH:28]=[C:23]([NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH:12]([C:16]2[CH:17]=[CH:18][C:19]([I:22])=[CH:20][CH:21]=2)[CH2:13][CH:14]=[CH2:15])[CH:24]=[C:25]([Cl:30])[CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69595261HCID 69595261, compound

Product 1

HCID 22177252HCID 22177252, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3,5-dichloro-phenyl)-{2-[2-(4-iodophenyl)-pent-4-enylamino]-ethyl}-carbamic acid tert-butyl ester (0.493 g, 0.85 mmol) in CH2Cl2 (20 mL) at 0° C. was added TFA (5 mL). The mixture was stirred and warmed to room temperature for 4 h. The solvent was removed by rotary evaporation and the residue was dissolved in EtOAc and washed twice with NaHCO3 (10% in H2O). The organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation to give N-(3,5-dichloro-phenyl)-N′-[2-(4-iodo-phenyl)-pent-4-enyl]-ethane-1,2-diamine (0.386 g, 0.81 mmol, 95%) as a brown oil. 1H NMR (300 MHz, CDCl3): δ 7.73 (d, 2H), 7.03 (d, 2H), 6.56 (t, 1H), 6.50 (d, 2H), 5.75 (m, 1H), 5.08 (m, 2H), 4.42 (br s, NH), 3.15 (m, 2H), 3.40 (m, 5H), 2.44 (m, 2H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed twice with NaHCO3 (10% in H2O)
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b4d161d651144c658f74e4112c65ad6b
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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