Hydrochloric Acid → HCID 22612279, compound

HRID 844034Notes

Reaction equation

HRID 844034 reaction equation
[CH3:1][N:2]([CH3:19])[C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH2:24].O.ON1C2C=CC=CC=2N=N1.Cl.[Cl-].C(N=C=N)C.Cl>CN(C)C=O.O.C(OCC)C>[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH:24][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[N:15][C:7]=1[O:6][C:5]1[CH:16]=[CH:17][CH:18]=[C:3]([N:2]([CH3:1])[CH3:19])[CH:4]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 666482-ChlorobenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 22612241HCID 22612241, compoundHCID 86758006HCID 86758006, compound

Product 1

HCID 22612279HCID 22612279, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution 2-(3-Dimethylamino-phenoxy)-nicotinic acid (0.200 grams, 0.775 mmole), 2-Chloro-benzylamine (0.120 grams, 0.85 mmole), and 1-hydroxybenzotriazole hydrate (0.126 grams, 0.93 mmole) in dry dimethylformamide (4 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide chloride hydrochloride (0.193 grams, 1.00 mmole) and stirred over night. The mixture was diluted with 50 ml water and extracted with ethyl acetate. The combined organics were washed with 1N NaOH, water and brine, dried over Na2SO4, filtered and concentrated to give an oil that was purified by chromatography on silica gel. Recrystalization from ethyl acetate/hexane gave an oil. The product was dissolved in diethyl ether and hydrochloric acid (g) was used to precipitate the salt, which was filtered, dissolved in methylene chloride and concentrated to a solid (0.075 g). M.P. 85-87° C.; Anal. calcd. for C21H20N3O2Cl.HCl: C, 60.30; H, 5.06; N, 10.04. Found: C, 60.58; H, 5.60; N, 9.28.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with 1N 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 gel
  8. customRecrystalization from ethyl acetate/hexane
  9. customgave an oil
  10. customto precipitate the salt, which
  11. filtrationwas filtered
  12. dissolutiondissolved in methylene chloride
  13. concentrationconcentrated to a solid (0.075 g)

Sources & evidence

ORD record
ord-447fa11354344690a69a3e6cf09f360e
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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