Triethylamine → HCID 15030209, compound

HRID 1655560Notes

Reaction equation

HRID 1655560 reaction equation
[CH3:1][CH:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH:12]=2)[CH:7]=1)[C:3]([OH:5])=O.[CH3:28][O:29][NH3+:30].[Cl-].C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1>[CH3:28][O:29][NH:30][C:3](=[O:5])[CH:2]([CH3:1])[C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH:12]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11639O-methylhydroxylammonium chlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 117258702-[6-[(Quinolin-2-yl)methoxy]naphthalen-2-yl]propanoic acid

Product 1

HCID 15030209HCID 15030209, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of the acid of Example 1 (2.32 g, 6.5 mmol), 0-methylhydroxylamine hydrochloride (0.54 g, 6.5 mmol) and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (1.25 g, 6.5 mmol) in tetrahydrofuran (100 ml) is added triethylamine (2.0 ml, 2 equiv). After overnight stirring at room temperature, the solvent is removed and methylene chloride is added. This is followed by sequential washings with 0.05N hydrochloric acid and water (2x). After drying over magnesium sulfate, the solvent is removed to afford a crude solid which is recrystallized from ethyl acetate to afford a white crystalline solid, 0.6 g(24%), m.p. 162°-164° C.

Workup

  1. customthe solvent is removed
  2. additionmethylene chloride is added
  3. washThis is followed by sequential washings with 0.05N hydrochloric acid and water (2x)
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent is removed
  6. customto afford a crude solid which
  7. customis recrystallized from ethyl acetate
  8. customto afford a white crystalline solid, 0.6 g(24%), m.p. 162°-164° C.

Sources & evidence

ORD record
ord-81c1c36ed3964f3b965bfa807758f148
Source dataset
uspto-grants-1993_10
Patent number
US05250693

Reaction notes

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