1-Hydroxybenzotriazole → HCID 178489891, compound

HRID 599544Notes

Reaction equation

HRID 599544 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-dd2a00130a7e48faafb7eeb147552b7c
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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