Diisopropylethylamine → HCID 86722591, compound

HRID 1503068Notes

Reaction equation

HRID 1503068 reaction equation
[Br:1][C:2]1[CH:12]=[C:11](/[CH:13]=[CH:14]/[CH:15]([C:20]2[CH:25]=[C:24]([Cl:26])[C:23]([Cl:27])=[C:22]([Cl:28])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])[CH:10]=[CH:9][C:3]=1[C:4]([N:6](C)[NH2:7])=[O:5].[F:29][C:30]([F:36])([F:35])[CH2:31][C:32](O)=[O:33].[CH3:37]CN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>ClCCCl.CN(C1C=CN=CC=1)C.O>[Br:1][C:2]1[CH:12]=[C:11](/[CH:13]=[CH:14]/[CH:15]([C:20]2[CH:21]=[C:22]([Cl:28])[C:23]([Cl:27])=[C:24]([Cl:26])[CH:25]=2)[C:16]([F:17])([F:19])[F:18])[CH:10]=[CH:9][C:3]=1[C:4]([NH:6][N:7]([CH3:37])[C:32](=[O:33])[CH2:31][C:30]([F:36])([F:35])[F:29])=[O:5]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27779723,3,3-Trifluoropropionic acidHCID 86722592HCID 86722592, compound

Product 1

HCID 86722591HCID 86722591, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of (E)-2-bromo-N-methyl-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzohydrazide (200 mg, 0.46 mmol) in DCE (15 mL), was added 3,3,3-trifluoropropanoic acid (59 mg, 0.38 mmol), DMAP (46 mg, 0.42 mmol), EDC.HCl (65 mg, 0.42 mmol) and DIPEA (0.2 mL, 1.16 mmol). The reaction mixture was stirred at 25° C. for 12 h, then diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 30% hexane:EtOAc) afforded the title compound as a yellow solid (50 mg, 25%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification
  6. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 30% hexane:EtOAc)

Sources & evidence

ORD record
ord-180a71d0873740e3bbd827e24862082a
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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