Hydrochloric Acid → HCID 86722569, compound

HRID 1503612Notes

Reaction equation

HRID 1503612 reaction equation
[Br:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=2)[C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.C(N=C=NCCCN(C)C)C.Cl.[NH2:40][C:41]1([C:44]#[N:45])[CH2:43][CH2:42]1.Cl>ClCCCl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:19]=[C:20]([Cl:26])[C:21]([Cl:25])=[C:22]([Cl:24])[CH:23]=2)[C:14]([F:17])([F:15])[F:16])[CH:8]=[CH:7][C:3]=1[C:4]([NH:40][C:41]1([C:44]#[N:45])[CH2:43][CH2:42]1)=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 86722549(E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid

Product 1

HCID 86722569HCID 86722569, compoundYield 11.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzoic acid (100 mg, 0.205 mmol) in DCE (10.0 mL) at RT was added 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC hydrochloride) (58.9 mg, 0.307 mmol), 1-amino-1-cyclopropanecarbonitrile hydrochloride (24.3 mg, 0.296 mmol), DMAP (catalytic) and TEA (22.79 mg, 0.225 mmol). The resulting reaction mixture was stirred at RT for 18 h. To the reaction mixture was added EtOAc (50 mL) and 0.1N HCl (10 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (1×). The combined organic layers were washed with aq NaHCO3 (1×), dried (MgSO4), filtered and concentrated under reduce pressure to give an oil. Purification by flash chromatography (SiO2, 230-400 mesh; eluting with 35% EtOAc in hexanes) afforded the title compound as a white solid (13 mg, 11.5%). Characterization data for this molecule is listed in Table 2.

Workup

  1. customThe resulting reaction mixture
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc (1×)
  4. washThe combined organic layers were washed with aq NaHCO3 (1×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customPurification
  10. washby flash chromatography (SiO2, 230-400 mesh; eluting with 35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-01c44186eda24be1ae04cb8bafa1f4ab
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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