2-Chlorobenzylamine → HCID 22612355, compound

HRID 844078Notes

Reaction equation

HRID 844078 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][CH:8]1[N:16](CC2C=CC=CC=2Cl)[CH:15]=[CH:14][CH:13]=[C:9]1[C:10]([OH:12])=O)(=[O:3])[NH2:2].[Cl:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C>CN(C)C=O.O>[C:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:32][CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=1[Cl:28])=[O:12])(=[O:3])[NH2:2]

Participants

7

Reactant 4

HCID 666482-ChlorobenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 21883477Ethylcarbodiimide hydrochlorideHCID 22612299HCID 22612299, compound

Product 1

HCID 22612355HCID 22612355, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-(3-Carbamoyl-phenoxy)-N-(2-chloro-benzyl)-nicotinic acid (0.300 grams, 1.25 mmole), o-chlorobenzylamine (0.195 grams, 1.375 mmole), and 1-hydroxybenzotriazole hydrate (0.203 grams, 1.50 mmole) in dry dimethylformamide (3 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.311 grams, 1.63 mmole) and stirred over night. The mixture poured into 100 ml water 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 a white solid that was purified by chromatography on silica gel eluting with 7% methanollmethylene chloride. Recrystalization from ethyl acetate/hexane gave a white solid (0.239 g). M.P. 153-155° C.; Anal. calcd. for C20H16N3O3Cl: C, 62.91; H, 4.22; N, 11.01. Found: C, 62.92; H, 4.30; N, 11.09.

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 a white solid
  7. customthat was purified by chromatography on silica gel eluting with 7% methanollmethylene chloride
  8. customRecrystalization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0842750446924c8dbb1480faac461375
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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