Triethylamine → HCID 11999006, compound

HRID 2102752Notes

Reaction equation

HRID 2102752 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3CCCNC3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:30][CH2:29][N:28]([C:33]([C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[O:40])[CH2:31][CH2:32]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 417436Pyridine-4-carbonyl chlorideHCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

Product 1

HCID 11999006HCID 11999006, compound

Conditions

Temperature
60 °C

Procedure

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one (50 mg, 0.13 mmol) (from Example 25a supra) in tetrahydrofuron (2 mL) was added triethyl amine (20.2 mg, 0.19 mmol) (Aldrich), followed by the addition of isonicotinoyl chloride (28.5 mg, 0.16 mmol) (Aldrich). The mixture was heated at 60° C. for 14 hours and then cooled down to room temperature. The solvent was removed and the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over MgSO4 and concentrated. The residue was purified by chromatography to give rac-6-chloro-3-(3-chloro-benzyl)-3-{1-(pyridine-4-carbonyl)-piperidin-4-yl}-1,3-dihydro-indol-2-one as a white solid. (Yield 31 mg, 48.4%).

Workup

  1. temperaturecooled down to room temperature
  2. customThe solvent was removed
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-50ce02910c3e497597deb3d5d29db991
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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