1-Hydroxybenzotriazole → HCID 178489891, compound

HRID 2235674Notes

Reaction equation

HRID 2235674 reaction equation
C1C=CC2N(O)N=NC=2C=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[NH:22][C:21](/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]4)=[C:27]([O:37][CH3:38])[CH:26]=3)=[N:20][C:19]=2[C:39]([OH:41])=O)=[CH:14][CH:13]=1.Cl.[Cl:43][CH2:44][CH2:45][NH2:46].C(N(C(C)C)CC)(C)C.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[Cl:43][CH2:44][CH2:45][NH:46][C:39]([C:19]1[N:20]=[C:21](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][C:28]([N:31]3[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]3)=[C:27]([O:37][CH3:38])[CH:26]=2)[NH:22][C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1)=[O:41]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 97937372-Chloroethylamine hydrochlorideHCID 86585896Sodium bicarbonate waterHCID 178489893HCID 178489893, compound

Product 1

HCID 178489891HCID 178489891, compoundYield 16.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBT (65 mg) and EDC (92 mg) were sequentially added to a solution of 5-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-1H-imidazole-4-carboxylic acid (100 mg), 2-chloroethylamine hydrochloride (56 mg) and IPEA (0.25 mL) in DMF (3 mL). The reaction solution was stirred at room temperature for two hours. Then, 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 (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1) to obtain 19 mg of the title compound. The property values of the compound are 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 (carrier: Chromatorex™ NH; elution solvent: ethyl acetate->ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-7ac42fd92a86428f87786ae65c9b926b
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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