1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 86722760, compound

HRID 587779Notes

Reaction equation

HRID 587779 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[CH:10]([C:15]2[CH:20]=[C:19]([Cl:21])[C:18]([Cl:22])=[C:17]([Cl:23])[CH:16]=2)[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[C:24]1[O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[N:28]=1.Br[C:33]1C=C(/C=C/C(C2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)C=[CH:44][C:34]=1[C:35]([NH:37]C(C)(C)C(O)=O)=O.[CH3:64]CN=C=NCCCN(C)C.Cl>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[CH:10]([C:15]2[CH:16]=[C:17]([Cl:23])[C:18]([Cl:22])=[C:19]([Cl:21])[CH:20]=2)[C:11]([F:14])([F:13])[F:12])[CH:5]=[CH:4][C:3]=1[C:24]([NH:28][C:27]([CH3:29])([CH3:30])[C:26]([NH:37][CH2:35][C:34]([CH3:44])([CH3:64])[CH3:33])=[O:31])=[O:25]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86722758(E)-2-(2-Bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)-4,4-dimethyloxazol-5(4H)-oneHCID 86722759HCID 86722759, compound

Product 1

HCID 86722760HCID 86722760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(E)-2-(2-Bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)-4,4-dimethyloxazol-5(4H)-one: A 25 mL round bottomed flask was charged with (E)-2-(2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzamido)-2-methylpropanoic acid (400 mg, 0.70 mmol), CH2Cl2 (10 mL) and stirred at 0° C. EDC.HCl (134 mg, 0.70 mmol) was added in one portion as a solid and the reaction mixture was allowed to warm toward ambient temperature and continued to stir for 1 h. The reaction was diluted with CH2Cl2, washed with brine, dried over MgSO4, filtered and evaporated to give a dark oil. The crude product was purified via flash chromatography eluting with 50% hexanes/CH2Cl2 to afford the title compound as an off white foam (220 mg, 57): 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.1 Hz, 1H), 7.73 (d, J=1.6 Hz, 1H), 7.42 (d, J=7.8 Hz, 3H), 6.56 (d, J=15.9 Hz, 1H), 6.45 (dd, J=15.9, 7.7 Hz, 1H), 4.12 (p, J=8.5 Hz, 1H), 1.57 (s, 6H); 19F NMR (376 MHz, CDCl3) δ −68.55; ESIMS m/z 554 ([M−H]−).

Workup

  1. temperatureto warm toward ambient temperature
  2. stirringto stir for 1 h
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a dark oil
  8. customThe crude product was purified via flash chromatography
  9. washeluting with 50% hexanes/CH2Cl2

Sources & evidence

ORD record
ord-e01261e950114e138daea8ba95fa8128
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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