Hydrochloric Acid → HCID 86722590, compound

HRID 1503067Notes

Reaction equation

HRID 1503067 reaction equation
Cl.[Br:2][C:3]1[CH:20]=[C:19](/[CH:21]=[CH:22]/[CH:23]([C:28]2[CH:33]=[C:32]([Cl:34])[C:31]([Cl:35])=[C:30]([Cl:36])[CH:29]=2)[C:24]([F:27])([F:26])[F:25])[CH:18]=[CH:17][C:4]=1[C:5]([NH:7][N:8](C)[C:9](OC(C)(C)C)=O)=[O:6]>O1CCOCC1>[Br:2][C:3]1[CH:20]=[C:19](/[CH:21]=[CH:22]/[CH:23]([C:28]2[CH:29]=[C:30]([Cl:36])[C:31]([Cl:35])=[C:32]([Cl:34])[CH:33]=2)[C:24]([F:26])([F:27])[F:25])[CH:18]=[CH:17][C:4]=1[C:5]([NH:7][NH:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86722589HCID 86722589, compound

Product 1

HCID 86722590HCID 86722590, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4M in dioxane) 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)benzoyl)-1-methylhydrazinecarboxylate (1.0 g 1.6 mmol) in 1,4-dioxane (100 mL). The reaction mixture was stirred at ambient temperature for 4 h. The volatiles were evaporated and the residue was triturated with ether to afford the title compound as a light yellow solid (660, 99%): 1H NMR (300 MHz, DMSO-d6) δ11.8 (s, 1H), 8.02 (s, 1H), 7.91 (s, 2H), 7.68 (d, J=9.3 Hz, 2H), 7.52 (d, J=8.1 Hz, 1H), 7.07 (dd, J=15.6, 9.3 Hz, 1H), 6.78 (d, J=15.3 Hz, 1H), 4.89-4.83 (m, 1H), 2.81 (s, 3H); ESIMS m/z 517.0 ([M+H]+).

Workup

  1. customThe volatiles were evaporated
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-b85ea715b5b04889bffea6ca3b64973e
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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