Triethylamine → HCID 23090937, compound

HRID 1820013Notes

Reaction equation

HRID 1820013 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[C:8]([F:15])[CH:7]=2)[CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[N:22]1([CH:28]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][NH2:38])=[CH:32][CH:31]=2)[CH3:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>CN(C)C=O.O1CCCC1.O>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([NH:38][CH2:37][CH2:36][C:33]3[CH:32]=[CH:31][C:30]([CH:28]([N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[CH3:29])=[CH:35][CH:34]=3)=[O:12])=[C:8]([F:15])[CH:7]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 23090959HCID 23090959, compoundHCID 57890415HCID 57890415, compound

Product 1

HCID 23090937HCID 23090937, compoundYield 46.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(cyclopropylmethoxy)-2-fluorobenzoic acid (242 mg, 1.15 mmol) and dimethylformamide (1 drop) in tetrahydrofuran (3 ml) was added dropwise oxalyl dichloride (113 μl, 1.30 mmol) at 0° C., and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure and the obtained residue was dissolved in tetrahydrofuran (3 ml). The solution was added dropwise to a solution of 2-{4-[1-(1-piperidinyl)ethyl]phenyl}ethylamine (310 mg, 1.02 mmol) obtained in Reference Example 15 and triethylamine (558 μl, 4.00 mmol) in tetrahydrofuran (2 ml) at 0° C., and the mixture was stirred at room temperature for 3 hrs. Water was added to the reaction mixture. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate) to give the title compound (200 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in tetrahydrofuran (3 ml)
  3. stirringthe mixture was stirred at room temperature for 3 hrs
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure
  8. customthe obtained residue was purified by NH-silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-8d3eca6fb291416fbc22c5817f205cee
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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