1-Hydroxybenzotriazole hydrate → HCID 22612231, compound

HRID 844068Notes

Reaction equation

HRID 844068 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:8][C:9]2[N:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:2]=1.O.ON1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.[ClH:29].C(N=[C:33]=[NH:34])C>CN(C)C=O.O.[OH-].[Na+]>[Cl:29][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:33][NH:34][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[N:17][C:9]=1[O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochlorideHCID 22612152HCID 22612152, compound

Product 1

HCID 22612231HCID 22612231, compoundYield 25.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-(Pyridin-3-ylmethoxy)-nicotinic acid (0.300 grams, 1.3 mmole) 2-Chloro-benzylamine (0.202 grams, 1.43 mmole), and 1-hydroxybenzotriazole hydrate (0.210 grams, 1.56 mmole) in dry dimethylformamide (10 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.324 grams, 1.69 mmole) and stirred over night. The mixture was diluted with 50 ml water and 50 ml 1N sodium hydroxide and extracted with ethyl acetate. The combined extracts were washed with 1 N NaOH, water and brine, dried over Na2SO4, filtered and concentrated to give an oil that was purified by chromatography on silica eluting with 5% methanol/methylene chloride. Recrystalization from ethyl acetate/hexane gave white crystals (0.116 g). M.P. 91-93° C.; Anal. calcd. for C19H16N3O2Cl: C, 64.50; H, 4.56; N, 11.88. Found: C, 64.38; H, 4.58; N, 11.97.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with 1 N NaOH, water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas purified by chromatography on silica eluting with 5% methanol/methylene chloride
  8. customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-49fbfb0d82fb4e23994f33c10c9b2423
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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