1-Hydroxybenzotriazole → HCID 86615147, compound

HRID 2235768Notes

Reaction equation

HRID 2235768 reaction equation
C1C=C[C:4]2[N:9](O)N=[N:7][C:5]=2C=1.C(N(C(C)C)CC)(C)C.[CH3:20][O:21][C:22]1[CH:23]=[C:24](/[CH:34]=[CH:35]/[C:36]([OH:38])=O)[CH:25]=[CH:26][C:27]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1.Cl.NCC#N>CN(C=O)C.O.C(OCC)(=O)C.C(Cl)CCl>[C:5]([CH2:4][NH:9][C:36](=[O:38])/[CH:35]=[CH:34]/[C:24]1[CH:25]=[CH:26][C:27]([N:28]2[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]2)=[C:22]([O:21][CH3:20])[CH:23]=1)#[N:7]

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11491918Aminoacetonitrile hydrochlorideHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid

Product 1

HCID 86615147HCID 86615147, compoundYield 54%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (4.48 g), HOBT (3.14 g) and IPEA (6.76 mL) were sequentially added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (2 g) and aminoacetonitrile hydrochloride (1.08 g) in DMF (25 mL), and the reaction solution was stirred at room temperature for five hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer washed with brine and then dried over anhydrous sodium sulfate and filtered through a silica gel pad (Chromatorex NH). The filtrate was concentrated under reduced pressure. The residue was crystallized (heptane-ethyl acetate-methanol system) to obtain 1.24 g of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a silica gel pad (Chromatorex NH)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was crystallized (heptane-ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-adcdc8bd90b84f13a5e477b0a8645bde
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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