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

HRID 599645Notes

Reaction equation

HRID 599645 reaction equation
C(N(C(C)C)CC)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Cl:25][CH2:26][CH2:27][CH2:28][CH:29]([C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:30]([OH:32])=O.Cl.Cl.[CH3:42][O:43][C:44]1[CH:45]=[C:46](/[CH:56]=[CH:57]/[C:58]([NH:60][NH2:61])=[O:59])[CH:47]=[CH:48][C:49]=1[N:50]1[CH:54]=[C:53]([CH3:55])[N:52]=[CH:51]1.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:42][O:43][C:44]1[CH:45]=[C:46](/[CH:56]=[CH:57]/[C:58]([NH:60][NH:61][C:30](=[O:32])[CH:29]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH2:28][CH2:27][CH2:26][Cl:25])=[O:59])[CH:47]=[CH:48][C:49]=1[N:50]1[CH:54]=[C:53]([CH3:55])[N:52]=[CH:51]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 66839298(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochlorideHCID 670673305-Chloro-2-(4-chlorophenyl)pentanoic acidHCID 86585896Sodium bicarbonate water

Product 1

HCID 670670895-chloro-2-(4-chlorophenyl)pentanoic acid N'-{(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazideYield 158.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

IPEA (6.02 mL) and BOPCl (1.79 g) were added to a solution of 5-chloro-2-(4-chlorophenyl)pentanoic acid (1.55 g) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochloride (2.03 g) in methylene chloride (80 mL), and the reaction solution was stirred at room temperature for two hours. Dichloromethane 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 then concentrated under reduced pressure to obtain 4.67 g of the title compound in an unrefined state. 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-752cd90c3e6c4cd39a1020781869dd2a
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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