1-Hydroxybenzotriazole → HCID 67067433, compound

HRID 1009365Notes

Reaction equation

HRID 1009365 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[Cl:21][CH2:22][CH2:23][CH2:24][CH:25]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[C:26]([NH:28][NH2:29])=[O:27].[CH3:37][O:38][C:39]1[CH:40]=[C:41](/[CH:51]=[CH:52]/[C:53](O)=[O:54])[CH:42]=[CH:43][C:44]=1[N:45]1[CH:49]=[C:48]([CH3:50])[N:47]=[CH:46]1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:37][O:38][C:39]1[CH:40]=[C:41](/[CH:51]=[CH:52]/[C:53]([NH:29][NH:28][C:26](=[O:27])[CH:25]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[CH2:24][CH2:23][CH2:22][Cl:21])=[O:54])[CH:42]=[CH:43][C:44]=1[N:45]1[CH:49]=[C:48]([CH3:50])[N:47]=[CH:46]1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 67067375HCID 67067375, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 67067433HCID 67067433, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (1.28 mL), HOBT (330 mg) and EDC (468 mg) were added to a solution of 5-chloro-2-(4-fluorophenyl)pentanoic acid hydrazide hydrochloride (342 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (315 mg) in DMF (5 mL), and the reaction solution was stirred at room temperature for 14 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 then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 427 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
  4. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-a5f2c9dad5364855b578a5bc627d226d
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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