1-Hydroxybenzotriazole → HCID 67067277, compound

HRID 599592Notes

Reaction equation

HRID 599592 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([CH2:32][CH2:33][OH:34])[C:28]([NH:30][NH2:31])=[O:29])=[CH:23][CH:22]=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39](/[CH:49]=[CH:50]/[C:51](O)=[O:52])[CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=[C:46]([CH3:48])[N:45]=[CH:44]1>CN(C=O)C.[Cl-].[Na+].O.C(OCC)(=O)C.C(Cl)CCl>[CH3:35][O:36][C:37]1[CH:38]=[C:39](/[CH:49]=[CH:50]/[C:51]([NH:31][NH:30][C:28](=[O:29])[CH:27]([C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[CH2:32][CH2:33][OH:34])=[O:52])[CH:40]=[CH:41][C:42]=1[N:43]1[CH:47]=[C:46]([CH3:48])[N:45]=[CH:44]1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 67067321HCID 67067321, compound

Product 1

HCID 67067277HCID 67067277, compoundYield 100.1%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

IPEA (0.17 mL), HOBT (134 mg) and EDC (190 mg) were added to a solution of 2-(4-fluorophenyl)-4-hydroxybutyric acid hydrazide (105 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (153 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for 14 hours. Ethyl acetate and brine 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 224 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-79810835226740b2a425f4b3e48ad9db
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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