1-Hydroxybenzotriazole → HCID 178522813, compound

HRID 1934727Notes

Reaction equation

HRID 1934727 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH2:4][CH2:3]1.[CH:21]1([CH2:27][NH2:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH:21]1([CH2:27][NH:28][C:11](=[O:13])[C:10]2[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:9]=2[NH:8][C@H:5]2[CH2:4][CH2:3][C@@H:2]([OH:1])[CH2:7][CH2:6]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 76688CyclohexanemethylamineHCID 178524575HCID 178524575, compound

Product 1

HCID 178522813HCID 178522813, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(cis-4-hydroxycyclohexylamino)-5-nitrobenzoic acid (120 mg), cyclohexanemethylamine (53.3 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimde hydrochloride (107 mg) and 1-hydroxybenzotriazole (81.0 mg) in anhydrous dimethylformamide (3 mL) was stirred for 18 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with 1N-hydrochloric acid, water, an aqueous saturated sodium bicarbonate solution and brine, successively, and dried over magnesium sulfate. After evaporation of the solvent, the residue was triturated with diisopropyl ether to give N-cyclohexylmethyl-2-(cis-4-hydroxycyclohexylamino)-5-nitrobenzamide (157 mg) as yellow powders.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed with 1N-hydrochloric acid, water
  3. dry with materialan aqueous saturated sodium bicarbonate solution and brine, successively, and dried over magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-4c7093f33af2416e9766831054ee7f47
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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