Ammonium Chloride → 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

HRID 546676Notes

Reaction equation

HRID 546676 reaction equation
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.Cl.[Cl:26][CH2:27][CH2:28][CH2:29][CH:30]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C:31]([NH:33][NH2:34])=[O:32].[F:44][C:45]1[CH:50]=[C:49]([N:51]2[CH:55]=[C:54]([CH3:56])[N:53]=[CH:52]2)[C:48]([O:57][CH3:58])=[CH:47][C:46]=1/[CH:59]=[CH:60]/[C:61](O)=[O:62].[Cl-].[NH4+]>C(Cl)Cl.C(OCC)(=O)C>[F:44][C:45]1[CH:50]=[C:49]([N:51]2[CH:55]=[C:54]([CH3:56])[N:53]=[CH:52]2)[C:48]([O:57][CH3:58])=[CH:47][C:46]=1/[CH:59]=[CH:60]/[C:61]([NH:34][NH:33][C:31](=[O:32])[CH:30]([C:35]1[CH:36]=[C:37]([F:43])[C:38]([F:42])=[C:39]([F:41])[CH:40]=1)[CH2:29][CH2:28][CH2:27][Cl:26])=[O:62]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66839107HCID 66839107, compoundHCID 668392315-Chloro-2-(3,4,5-trifluorophenyl)pentanoic acid hydrazide hydrochloride

Product 1

HCID 668395365-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazideYield 103.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.31 mL) and BOPCl (119 mg) were added to a solution of 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid hydrazide hydrochloride (114 mg) and (E)-3-[2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (99 mg) in methylene chloride (5 mL), and the reaction solution was stirred at room temperature for one hour. Ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 200 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20531ba26a4b4890ad9c61aa4b5b3a19
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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