Diisopropylethylamine → 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]acryloyl}hydrazide

HRID 1009375Notes

Reaction equation

HRID 1009375 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].[CH3:44][O:45][C:46]1[CH:47]=[C:48](/[CH:58]=[CH:59]/[C:60](O)=[O:61])[CH:49]=[N:50][C:51]=1[N:52]1[CH:56]=[C:55]([CH3:57])[N:54]=[CH:53]1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:44][O:45][C:46]1[CH:47]=[C:48](/[CH:58]=[CH:59]/[C:60]([NH:34][NH:33][C:31](=[O:32])[CH:30]([C:35]2[CH:36]=[C:37]([F:43])[C:38]([F:42])=[C:39]([F:41])[CH:40]=2)[CH2:29][CH2:28][CH2:27][Cl:26])=[O:61])[CH:49]=[N:50][C:51]=1[N:52]1[CH:56]=[C:55]([CH3:57])[N:54]=[CH:53]1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 668392315-Chloro-2-(3,4,5-trifluorophenyl)pentanoic acid hydrazide hydrochlorideHCID 66839567(E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]acrylic acidHCID 86585896Sodium bicarbonate water

Product 1

HCID 668395195-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]acryloyl}hydrazide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.14 mL) and BOPCl (100 mg) were added to a solution of 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid hydrazide hydrochloride (83 mg) and (E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]acrylic acid (CAS No. 870837-77-7, 68 mg) in methylene chloride (5 mL), and the reaction solution was stirred at room temperature for 18 hours. Ethyl acetate and saturated sodium bicarbonate water 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 112 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-c612978cd06a47d2976eee414270a5ec
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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